Total Synthesis of Oxazolomycin A
|
|
|
- Mabel Townsend
- 5 years ago
- Views:
Transcription
1 Total Synthesis of xazolomycin A Me xazolomycin A Me Eto, K.; Yoshino, M.; Takahashi K.; Ishihara, J.; atakeyama S. rg. Lett. 2011, 13, 5398 Dimas Paz Wipf group- Current Literature ctober 8, 2011 Dimas Wipf Group Page 1 of 14 12/28/2011
2 xazolomycin A - Isolation and Biological Active xazolomycin A was isolated from a strain Streptomyces together with eooxazolomycin in 1985 by Uemura at al. xazole polyene lactam-lactone xazolomycin A Me Me eooxazolomycin Me They exhibit wide ranging and potent antibacterial and activities as well as in vivo antitumor activity. a) Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; akano, F.; Matsuzaki, A. Tetrahedron Lett. 1985, 26, b) Takahashi, K.; Kawabata, M.; Uemura, D.; Iwadare, S.; Mitomo,R.; akano, F.; Matsuzaki, A. Tetrahedron Lett. 1985, 26, Moloney, M. G.; Trippier, P. C.; Yaqoob, M.; Wang, Z. Curr. Drug. Discovery Technol. 2004, 1, 181 Dimas Wipf Group Page 2 of 14 12/28/2011
3 Retrosynthesis Bn Me C 2 Me C 2 Me Me xazolomycin A Me Bn Conia-ene type cyclization C 2 Me C 2 Me Me Amidation Me Dihydroxylation ozaki-iyama-kishi Me Bn C 2 Me Me Fmoc I P Me P P Me Dimas Wipf Group Page 3 of 14 12/28/2011
4 Synthesis of the γ-lactone Bn Me TBDPS + Bn Tf 1. n-buli, DMPU/TF!78 C 2. TBAF, TF 81% (2 steps) Bn 1. 2 Cr 4, aq acetone, 0 C 2. SCl 2, C 2 Cl 2 3. toluene C 2 Me Me C 2 Me 63% (3 steps) Bn Me C 2 Me C 2 Me In(Tf) 3 (5 mol%) DBU (4.4 mol%) toluene, reflux 91% Bn C 2 Me C 2 Me Me nyango, E..; Tsurumoto, J.; Imai,.; Takahashi, K.; Ishihara, J.; atakeyama, S. Angew. Chem. Int. Ed. 2007, 46, Dimas Wipf Group Page 4 of 14 12/28/2011
5 Plausible mechanism - In(III)-catalyzed Conie-ene type cyclization Endo, K.; atakeyama, T; akamura, M.; akamura, E. J. Am. Chem. Soc. 2007, 129, 5264 Dimas Wipf Group Page 5 of 14 12/28/2011
6 Bn Synthesis of the γ-lactone C 2 Me C 2 Me s 4, M Me TF- 2 Bn 100% C 2 Me Me Bn Me 1. Li, TF then Cl (1 M) 2. (CCl) 2, DMF (cat.), C 2 Cl 2 then ab 4, TF-Me!78 C, 60% Bn Me 17 was supported by ESY spectrum in [D 8 ]TF/D 2 and also suggested to be energetically most stable by Molecular mechanics calculation. Dimas Wipf Group Page 6 of 14 12/28/2011
7 Synthesis of the right-hand segment P Me P P Me Bn 1. MMCl, i-pr 2 Et, C 2 Cl 2 Me 2. ab 4, TF-Et 3. TBSTf, 2,6-lutidine C 2 Cl 2,!78 C 93% (3 steps) Bn TBS MM Me Me 3 + BF 4 - proton sponge 4 Å MS, C 2 Cl 2 95% Me Bn ZrCl 4, i-pr reflux TBS MM Me Me Bn 1. TBAF, TF 2. 2 Cr 4, acetone, 0 C Me 3. acl 2, a 2 P 4 2-methyl-2-butene t-bu- 2 n-c SC 2 TIPS CuBr 2, n-bu 4 Br Bn Me Et 3, 4 Å MS, C 2 Cl 2 67% (5 steps) Bn Me MM Me TIPS Me Dimas Wipf Group Page 7 of 14 12/28/2011
8 Synthesis of the right-hand segment Bn Me TIPS Me i-pr 2 Si(Tf) 2, 2,6-lutidine ClC 2 C 2 Cl, reflux, 90% Bn Me Si TIPS Me P Me P P Me TIPS 1. 2, Pd() 2, AcEt 2. Dess-Martin periodinane ac 3, C 2 Cl 2 92% (2 steps) Me Si Me Synthesis of the middle segment Fmoc I 2 FmocCl ac 3 dioxane 96% Fmoc acrolein oveyda-grubbs 2nd C 2 Cl 2, 85% Fmoc C CrCl 2, CI 3 TF Fmoc I 68% (E:Z = 8:1) Dimas Wipf Group Page 8 of 14 12/28/2011
9 Synthesis of the left-hand segment Me Ac EtCCl, LiCl 4, i-pr 2 Et C 2 Cl 2 -Et 2, -78 C, 92% 98% ee, >99% de Plausible mechanism C R 3 * R 1 R 3 * + M R 1 Lewis acid M (M) R 3 * R 1 R 2 C R 3 * = Me M R 1 R 2 M R 1 R 2 R 1 R 2 R 3 * R 3 * Zhu, C.; Shen, X.; elson, S. C. J. Am. Chem. Soc. 2004, 126, 5352 Dimas Wipf Group Page 9 of 14 12/28/2011
10 Synthesis of the left-hand segment Ac ame Me, 95% C 2 Me LDA, MeI TF,!20 C 84% C 2 Me 1. ame, Me 2. TBSTf 2,6-lutidine, C 2 Cl 2 0 C, 98% (2 steps) TBS C 2 Me 1. n-buli, I 2, TF,!78 C 2. o-( 2 )C 6 4 S 2 2 Et 3, i-pr-tf 92% (2 steps) I TBS C 2 Me Pd(PPh 3 ) 4, CuI CsF, DMF 1. F, MeC 2. Li, TF- Me 83% SnBu 3 TBS Me 3. Ac 2, pyridine ac 3, Me 88% Ac Dimas Wipf Group Page 10 of 14 12/28/2011
11 Synthesis of the left-hand segment Ac Et Et 1. KSC, Cl, MeC, reflux 2. K, n-bui, TF 79% (2 steps) BuS t-buli, CuC 2 LiCl TF,!78 C BrC 2 CCSiMe 3!78 C - rt, 94% BuS 1. Raney i, acetone: Et reflux, 92% 2. AgTf, C 2 Cl 2 /Me/ 2, 73% n-bu 3 Sn, AIB 70 C, 88% SnBu 3 E/Z = 6:1 Dimas Wipf Group Page 11 of 14 12/28/2011
12 Synthesis of xazolomycin A TIPS Ac Me Me Me Si Me Fmoc I Dimas Wipf Group Page 12 of 14 12/28/2011
13 Synthesis of xazolomycin A TIPS Me Si Me 1. icl, CrCl 2, TF-DMS Fmoc 2. Dess-Martin periodinane ac 3, C 2 Cl 2 3. L-selectride, TF,!78 C 53% (3 steps) I Fmoc Me TIPS 7R + 7S-epimer Pr Me Si Pr 4:1 1. Ac 2, pyridine, 91% 2. DBU, C 2 Cl 2 then BPCl, Et 3, C 2 Cl 2 68% (2 steps) Ac Ac Me Si TIPS Me 1. F pyridine, TF 2. Li, TF Ac ATU, i-pr 2 Et, TF 41% (3 steps) Me Me xazolomycin A Me Me Dimas Wipf Group Page 13 of 14 12/28/2011
14 Summary and utlook Me xazolomycin A Me xazolomycin A was synthesized in 34 steps of the longest linear sequence in 1.4% overall yield from methyl (S)-3-hydroxy-2-methylproprionate. Key transformation include In(III)-catalyzed Conia-ene type cyclization, Cinchona alkaloid-catalyzed cyclocondensation and asymmetric dihydroxylation. Dimas Wipf Group Page 14 of 14 12/28/2011
Syntheses of Leucascandrolide A. Supergroup Meeting August 4 th, 2004 Yu Yuan
Syntheses of Leucascandrolide A Supergroup Meeting August 4 th, 2004 Yu Yuan Leucascandrolide A Me Me Me Dambrosio, M.; Guerriero, A.; Debitus, C.; Pietra, F. elvetica Chimica Acta 1996, 79, 51-60 Me 1
Total Syntheses of Nominine
Total Syntheses of ominine i Literature t Group eting Lizzie Bryan ctober 17, 2007 Aconite Alkaloids Atidane V eatchane Cycloveatchane Aconitane etisan Muratake,. M.; atsume, M.; akai,. Tetrahedron, 2006,
Prof. Ang Li. Literature Seminar Kosuke Minagawa (D2)
Prof. Ang Li Literature Seminar 2017. 10. 28 Kosuke Minagawa (D2) 1 2 3 aspidodasycarpine 1) 2 C sespenine 3) atural Products Synthesized by Ang Li group clostrubin 6) drimentine A 7) i-bu rubriflordilactone
Highly Cytotoxic, Structure Similar Polyke>des CO 2 H
Current Literature Anguinomycins and Deriva2ves: Total Syntheses, Modeling, and Biological Evalua2on of the Inhibi2on of Nucleocytoplasmic Transport liv Eidam, Ulrike Kutay, Karl Gadermann, et al, JACS,
Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132,
Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132, 7876 7877. Current Literature Presentation 10JUL2010 Michael Yang Mike Yang @ Wipf Group Page 1 of 15 7/10/2010 Sieboldine A Background
Total Syntheses of Minfiensine
Total Syntheses of Minfiensine Douany, A. B.; umphreys, P. G.; verman, L. E.*; Wrobelski, A. D., J. Am. Chem. Soc. 2008, ASAP. D: 10.1021/ja800163v Shen, L.; Zhang, M.; Wu, Y.; Qin, Y.*, Angew. Chem. nt.
Total Synthesis of (-)-Mersicarpine
Total Synthesis of (-)-Mersicarpine Rie akajima, Tsuyoshi gino, Satoshi Yokoshima, and Tohru Fukuyama. J. Am. Chem. Soc. ASAP Published online 1-7-2010 Eric E. Buck Current Literature January 23, 2010
Approaches to the Synthesis. of Tetrahydropyrans. (and closely related heterocycles)
Approaches to the Synthesis of Tetrahydropyrans (and closely related heterocycles) William Morris Literature Presentation July 6, 2004 I. Intro A Nomenclature B Prevalence in Nature C Biosynthetic Considerations
Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization
![Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization](/thumbs/82/85235286.jpg "Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization")
Total Synthesis of (+/-)-Goniomitine via a Formal itrile/donor-acceptor Cyclopropane [3 + 2] Cyclization (-)-Goniomitine Christian L. Morales and Brian Pagenkopf* rganic Letters, ASAP Current Literature
Enantioselective Synthesis of (+)-Cephalostatin 1
1 Cephalostatin 1 Enantioselective Synthesis of (+)-Cephalostatin 1 Tingting Mo Wipf Group Current Lit. Dec. 26 2009 Tingting Mo @ Wipf Group Page 1 of 9 /28/2009 2 Background 1972, marine worm Cephalodiscus
SECTION 12. «POT-POURRI» in Organic Synthesis (2018)
SECTIN 12 «PT-PURRI» in rganic Synthesis (2018) 1 Total Synthesis of Erythromycin A via a Spiroketal ERYTRMYCIN A DESLNGCAMPS et al. Can. J. Chem. 1985, 63, 2810-2820. 2 Tetrahydropyran Derivative as Starting
A Concise Synthesis of ( )- Aplyviolene Facilitated by a Stragetegic Ter<ary Radical Conjugate Addi<on
A Concise Synthesis of ( )- Aplyviolene Facilitated by a Stragetegic Ter
Total Synthesis of the Proposed Structure of Briarellin J
Total Synthesis of the Proposed Structure of Briarellin J Michael T. Crimmins, Mark C. Mans, and Abimael D. Rodríguez. rg. Lett. 2010, ASAP Ac Ac originally proposed structure revised structure Eric E.
I. Liu Lab. Ka<e Boknevitz 1
A ighly Convergent Total Synthesis of Leustroducsin B Barry M. Trost,* Berenger Biannic, Cheyenne S. Brindle, B. Michael Keefe, Thomas J. unger, and Ming-Yu gai Department of Chemistry, Stanford University,
Total Synthesis of ( )-Virginiamycin M2
Total Synthesis of ( )-Virginiamycin M2 Jie Wu and James S. Panek, Angewandte Chemie International Edition, 2010, 49, 6165-6168 btained from the CDC Public ealth Image Library. Image credit: CDC/Dr. David
Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
ine-step nantioselective Total Synthesis of (+)-Minfiensine Jones, S. B.; Simmons, B.; MacMillan, D. W. C.* J. Am. Chem. Soc. 2009, ASAP. DI: 10.1021/ja906472m Kara George Wipf Group - Current Literature
A New Strategy for Efficient Synthesis of Medium and Large Ring Lactones without High Dilution or Slow Addition
A ew Strategy for Efficient Synthesis of Medium and Large ing Lactones without High Dilution or Slow Addition BF 3 Et 2 TIPS 2,4,6-collidine n + n+2 ' ' Zhao, W.; Li, Z; Sun, J. J. Am. Chem. Soc. 2013
Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine
Enantioselective Total Synthesis of (-)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine Julian A. Codelli, Angela L. A. Puchlopek, and Sarah E. Reisman* JACS. ASAP. ct. 24, 2011 DI: 10.1021/ja209354e
Studies Toward the Total Synthesis of (±)-Noelaquinone
Research Topic Seminar 18 June 2005 Studies Toward the Total Synthesis of (±)-Noelaquinone David Amantini WIPF GRUP The Role of Natural Products in Drug Discovery For thousands of years medicine and natural
Hennoxazole A. Philip Williams Group Meeting December 12, OMe. OMe 1 6 O H
ennoxazole A 1 6 11 17 24 Philip Williams Group eting December 12, 2007 Discovered Discovered by Paul cheuer at the University of awaii in 1991. Isolated 480mg ennoxazole A from 4.5kg from the sponge Polyfibrospongia
Massachusetts Institute of Technology Organic Chemistry 5.512
Massachusetts Institute of Technology rganic Chemistry 5.512 Problem Set 6 Solutions Stereocontrolled Carbonyl Reduction and Aldol Reactions May 5, 2006 Lucy Kohnen ( The target compound was used as an
Comparative Synthesis of Ingenol. Tyler W. Wilson SED Group Meeting
Comparative Synthesis of Ingenol Tyler W. Wilson SED Group eting 2.27.07 Ingenol: Biology, Isolation, and istory During WWII a latex was manufactured by precipitating the milky juice of the Euphorbia Ingen
Total Synthesis of ( )-Himandrine
Total Synthesis of ( )-imandrine M. Movassaghi,* M. Tjandra and J. Qi J. Am. hem. Soc. 2009, 131, 9648-9650 Bz Adam T. oye urrent Literature ctober 3, 2009 Adam oye @ Wipf Group Page 1 of 22 10/3/2009
Asymmetric Radical Reactions. Zhen Liu 08/30/2018
Asymmetric adical eactions Zhen Liu 08/30/2018 Contents Introduction eactions Using Chiral Auxiliary Chiral Lewis Acid-diated eactions Transition tal-catalyzed eactions eactions Using Chiral rganocatalysts
Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene-Alkene [2+2] Cycloadditions and Late Stage C-H Oxidation
![Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene-Alkene [2+2] Cycloadditions and Late Stage C-H Oxidation](/thumbs/94/118539468.jpg "Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene-Alkene [2+2] Cycloadditions and Late Stage C-H Oxidation")
Total Synthesis of Gracilioether F: Development and Application of Lewis Acid Promoted Ketene-Alkene [2+2] ycloadditions and Late Stage - xidation hristopher M. Rasik and M. Kevin Brown Angew. hem. Intd.
Stemona Alkaloids. tuberostemonol. OMe O O. neostemonine. OMe O O. protostemonine
I. Introduction 9 9a 8 1 2 The Stemonaceae plant family, which comprises over 0 species, produces a large class of structurally diverse alkaloids featuring a conserved pyrrolo [1,2-a] azepine = perhydroazaazulene
Synthetic Developments Towards the Preparation of Erythromycin and Erythronolide Derivatives
ynthetic Developments Towards the Preparation of Erythromycin and Erythronolide Derivatives Russell C. mith Denmark Group Meeting 8-9-2005 most extensive project in organic synthesis this phenomenon is
Keisuke Suzuki. Baran lab Group Meeting 6/11/16. Shigenobu Umemiya. Akira Suzuki. Takanori Suzuki (Hokkaido University)
197.D., Teruaki Mukaiyama, University of Tokyo 193 Assistant Professor, Keio University 197 Lecturer, Keio University 199 Assocate Professor, Keio University 1990 Visiting Professor, ET 1994 ull Professor,
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02
![Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02](/thumbs/93/114018431.jpg "Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates. Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02")
Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper Allenylidene Intermediates Reporter: Jie Wang Checker: Shubo Hu Date: 2016/08/02 Xiao, W.-J. et al. J. Am. Chem. Soc. 2016, 138, 8360.
Synthesis of Azadirachtin: A Long but Successful Journey
ynthesis of Azadirachtin: A Long but uccessful Journey Gemma E. Veitch, Edith Beckmann, Brenda J. Burke, Alistair Boyer, arah L. Maslen, and teven V. Ley Angew. Chem. Int. Ed. 2007, Early View And Gemma
Total Synthesis towards Maoecrystal V
Total Synthesis towards Maoecrystal V isolated from the leaves of a Chinese medicinal herb, Isodon eriocalyx in 2004. structure was determined by comprehensive NMR and MS spectroscopic analysis and confirmed
Studies toward the Synthesis of Azadirachtin: Total Synthesis of a Fully Functionalized ABC Framework and Coupling with a Norbornene Domain
Studies toward the Synthesis of Azadirachtin: Total Synthesis of a Fully Functionalized ABC Framework and Coupling with a Norbornene Domain Nicolaou and Co-workers Angew. Chem. Int. Ed. 2005, 44, 3443
Electrophilic Carbenes
Electrophilic Carbenes The reaction of so-called stabilized diazo compounds with late transition metals produces a metal carbene intermediate that is electrophilic. The most common catalysts are Cu(I)
A Review of Total Synthesis of Spirotryprostatin A and B. Jinglong Chen Supergroup meeting Princeton University June
A Review of Total Synthesis of Spirotryprostatin A and B Jinglong Chen Supergroup meeting Princeton University June 28 2006 ovel Mammalian Cell Cycle Inhibitors, Spirotryprostatins A and B Me Spirotryprostatin
Total Synthesis of (+)-Suaveolindole
1 Total Synthesis of (+)-Suaveolindole 15 2 C 16 11 Emile J. Velthuisen and Samuel J. Danishefsky J. Am. Chem. Soc. 2007, 9, 10640-10641 Julia Vargas September 15, 2007 2 utline Isolation and Elucidation
11-Step Enantioselective Synthesis of ( )-Lomaiviticin Aglycon
11-Step Enantioselective Synthesis of ( )-Lomaiviticin Aglycon Seth B. erzon, Liang Lu, Christina M. Woo, and Shivajirao L. Gholap J. Am. Chem. Soc. ASAP DI 10.1021/ja200034b Melissa Sprachman Current
"-Amino Acids: Function and Synthesis
"-Amino Acids: Function and Synthesis # Conformations of "-Peptides # Biological Significance # Asymmetric Synthesis Sean Brown MacMillan Group eting ovember 14, 2001 Lead eferences: Cheng,. P.; Gellman,
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization Denmark, S.E. and Collins, W.R. rg. Lett. 2007, 9, 3801-3804. C 2 H + Se Lewis Base CH 2 Cl 2 Se Presented
Synthesis of Resorcinylic Macrolides
Synthesis of Resorcinylic Macrolides X H H H H Cl X= Radicicol (1) X= CH2 Cycloproparadicicol (2) Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, ASAP Danishefsky, S. J. rg. Lett. 2004, 6, 413-416 Danishefsky,
Large-Scale Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide
61.7 g prepared in 39 steps 43 chemists worked on the project which lasted 20 months Chris Kendall @ Wipf Group 1 3/27/04 8 22 1 5 24 carbon linear polypropionate chain containing stereocenters (6 hydroxyl
Total Synthesis of Peloruside A Through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions
Total Synthesis of Peloruside A Through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions Thomas R. oye, Junha Jeon, Lucas C. Kopel, Troy D. Ryba, Manomi A. Tennakoon, and Yini
1.MsCl,Et 3 N CH 2 Cl 2,-10 C,97% 2.KOAc,H 2 O acetone, reflux, 82% 3.NaOH(1eq.) MeOH,-20 C,75% H H
Problem Session(4) 2018.04.21. Yinghua Wang Please provide each reaction mechanism. 1 Ac Ac 1.Ms,Et 3 C 2 2,-10 C,97% 2.KAc, 2 acetone, reflux, 82% 3.a(1eq.),-20 C,75% 4.DMP,C 2 2 5.basicAl 2 3,TF 83%(2
Literature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
Progress toward the Total Synthesis of Pleurotin
Progress toward the Total Synthesis of Pleurotin SINYA IIMURA Wipf Research Group Meeting July 9th, 2005 Shinya Iimura @ Wipf Group 1 7/10/2005 Presentation utline! Isolation and Structure! Biological
Synthesis of Amphidinolide X and an Exploration of Key Reactions
PJM 1/12/05 Synthesis of Amphidinolide X and an Exploration of Key eactions Lepage,.; Kattnig, E.; Furstner, A. JACS, 2004, 126, 15970-15971. 7 13 1 6 19 - Produced by marine dinoflagellates, Amphidinium
A Modular Approach to Polyketide Building Blocks: Cycloadditions of Nitrile Oxides and Homoallylic Alcohols
A Modular Approach to Polyketide Building Blocks: Cycloadditions of itrile xides and Homoallylic Alcohols rganic Letters, 2005, ASAP ina Lohse-Fraefel and Erick M. Carreira * H H H + ' 1. t-bucl, -78 C
Short Lit
Short Lit. - 7-12-2010 Jonathan A. Brekan a Department of Chemistry, orthwestern University, 2145 Sheridan Road, 60208, Evanston, Illinois, United States of America Citronellal Monoterpenoid distillate
Silenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin
lenes in organic synthesis: a concise synthesis of (±)-epi-picropodophyllin obert D. C. Pullin, Jonathan D. Sellars, and Patrick G. Steel* rg. Biomol. Chem., 2007, 5, 3201-3206 H H C Adam Hoye Current
Literature Report. A 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed Dehydro Diels-Alder Reaction
Literature Report 11-Steps Total Synthesis of Magellanine through a Gold(І)-Catalyzed ehydro iels-lder Reaction Reporter: ong-qiang Shen Checker: Cong Liu ate: 2017/06/19 McGee, P.; Bétournay, G.; Barabé,
Chiral Diol Promoted Boronates Addi3on Reac3ons. Lu Yan Morken Group Boston College
Chiral Diol Promoted Boronates Addi3on Reac3ons Lu Yan Morken Group Boston College Main Idea R R B or R R B Ar * exchange B * * or B Ar R 1 R 1 R 2 R 1 R 2 Products not nucleophilic enough nucleophilic
C-O C-O C-N A A. (KHMDS) C-N (scheme 1) C-O C-N (1)
C- C- C- A A 2007 2008 -t- (Boc)-- (MM)- () (KMDS) C- (scheme ) C- C- () C- C- C- C- C- C- B C- B (scheme 2) C- B (2) C- manzacidin A Manzacidine A (5) - ATP (fig. ) C- 5 Ph MM Boc ethyl lactate X n=,2
Convergent Route to ent-kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α6α- Diacetoxy-ent-kaura-9(11),16-dien- 12,15-dione
Convergent Route to ent-kaurane Diterpenoids: Total Synthesis of Lungshengenin D and 1α6α- Diacetoxy-ent-kaura-9(11),16-dien- 12,15-dione Xiangbo Zhao, Wu Li, Junjie Wang, and Dawei Ma* Shanghai Institute
Dr. P. Wipf Page 1 of 5 10/7/2009. Cl Ru. Kingsbury, J. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
Dr. P. Wipf Page 1 of 5 10/7/2009 Alkene Metathesis Grubbs II published The Catalysts Me Mo F 3C CF3 Me F 3C CF3 C(Me) 2 chrock, R. R.; Murdzek, J..; Bazan, G. C.; Robbins, J.; DiMare, M.; 'Reagan, M.
Enan$oselec$ve Total Synthesis of Amphidinolide F
Enan$oselec$ve Total Synthesis of Amphidinolide F Subham Mahapatra and ich G. Carter regon State University Angew. Chem. nt. Ed., 2012, 51, 7948 Nicolas Millius Bern, 07.02.2013 ntroduc$on isolated from
Nilson, M. G.; Funk, R. L. Org. Lett. 2010, ASAP. Chad Hopkins Wipf Group Literature Presentation
TtlS Total Synthesis of ( ) akadomarin kd A ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad opkins Wipf Group Literature Presentation 10 23 10 Chad opkins @ Wipf Group Page 1 of 11 12/5/2010 Isolation
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations Domingo Garcia-Cuadrado, Ana M. Cuadro, Bernado M. Barchin, Ana unez, Tatiana Caneque, Julio Alvarez-
Denmark Group Meeting. & Electrophilic rearrangement of amides
Denmark Group Meeting Palladium catalyzed Dearomatizationeaction & Electrophilic rearrangement of amides 11 th Bo Peng th Feb. 2014 1 https://maps.google.com 2 Palladium catalyzed Dearomatization eaction
Additions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
A Stereoselective Synthesis of (+)-Gonyautoxin 3
A Stereoselective Synthesis of (+)-Gonyautoxin 3 Mulcahy, J. V.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 12630-12631 Total Synthesis of (+)-Lithospermic Acid by Asymmetric Intramolecular Alkylation via
Towards Maoecrystal V: A Comparison of Recent Strategies
Towards Maoecrystal V: A Comparison of Recent Strategies Reactant/Reagent Current Literature: November 14, 2009 lissa Sprachman lissa Sprachman @ Wipf Group Page 1 of 14 12/28/2009 Maoecrystal V: Structural
Practical Synthesis of PC190723, an Inhibitor of the Bacterial Cell Division Protein FtsZ!
Practical ynthesis of PC190723, an Inhibitor of the Bacterial Cell Division Protein tsz! orto,. A.; lmstead, M. M.; haw, J. T. J. rg. Chem. 2010, 75, 7946.! Ammonia ynthons for the Multicomponent Assembly
Stereoretentive Suzuki-Muyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to ( )-Peridinin
Stereoretentive Suzuki-Muyaura Coupling of aloallenes Enables Fully Stereocontrolled Access to ( )-Peridinin 3' ' ' 5' 5 5 Ac Eric M. Woerly, Alan. Cherney, Erin K. Davis and Martin D. Burke J. Am. Chem.
Highlights of Schmidt Reaction in the Last Ten Years
ighlights of Schmidt eaction in the Last Ten Years Dendrobates histrionicus Jack Liu ov. 18, 2003 Introduction Classical Schmidt reaction of aldehydes and carboxylic acids Classical Schmidt reaction of
Total Synthesis of the Chartellines
Total Synthesis of the Chartellines X Y chartelline A, X = Y = chartelline B, X =, Y = chartelline C, X = Y = Mariam Shamszad ovember 1, 2006 Background Chartellines A, B, and C were isolated in the 1980s
JOC Year-in-Review, 1984
Baran Lab Group eting JC Year-in-eview, 198 Y oshihiro Ishihara Statistics for J. rg. Chem. 198, Volume 9, Issues 1-26: 1313 Papers 1 erbert C. Brown 8 Albert Padwa 8 Leo A. Paquette 7 Dale L. Boger 7
Chiral Brønsted Acid Catalysis
Chiral Brønsted Acid Catalysis Aryl Aryl Aryl Aryl S CF 3 2 P Fe CF 3 CF 3 2 Jack Liu ov. 16, 2004 CF 3 Introduction Chiral Brønsted acid catalysis in nature: enzymes and peptides Chiral Brønsted acid
Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic
Journal Club (3) Tomoya akamura Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic Justin T. Malinowski, Robert J. Sharpe, Jeffrey S. Johnson Science 03, 30, 80 8.. Introduction -.
Catalytic Reactions in Organic Synthesis
17 April, 2008 Catalytic eactions in rganic Synthesis hodium Complexes and edox Catalysts Koichi AASAKA, Motoki YAMAE, Shunsuke CIBA Division of Chemistry and Biological Chemistry, School of ysical and
Problem session (3) Daiki Kuwana. Please fill in the blank and explain reaction mechanisms and stereoselectivities.
Problem session (3) Daiki Kuwana Please fill in the blank and explain reaction mechanisms and stereoselectivities. 1. 1-1 1. (Ac) 2 (10 mol%), DPEphos (20 mol%) Et 3, toluene, 90 C 2. s 4 (14 mol%), M;
CEM 852 Exam LDA, THF, 0 C, 15 min; then
CEM 85 Exam- April, 005 This exam consists of 5 pages. Please write ALL your answers in the answer books. Please write legibly and draw all structures clearly. Good luck. 1. Provide examples of the following
JOC: 1985 Year in Review
Baran Group eting JC: 1985 Year in eview Syntheses discussed: thodoligies discussed: Quadrone 2 C (+)-irsutic Acid C (±) Coriolin (!)-Longifolene (!)-astanecine Manganese (III)-mediated "-lactone annulation
Short Literature Presentation 10/4/2010 Erika A. Crane
Copper-Catalyzed Enantioselective Synthesis of trans-1- Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Additions-Intramolecular Enolate Trapping artog, T. D.; Rudolph, A.; Macia B.; Minnaard, A.
Synthesis of the HCV Protease Inhibitor Vaniprevir (MK- 7009) Using Ring-Closing Metathesis Strategy
ynthesis of the CV Protease Inhibitor Vaniprevir (MK- 7009) Using Ring-osing Metathesis trategy Jongrock Kong*, Cheng-yi Chen*, Jaume Balsells-Padros, Yang Cao, Robert F. Dunn, arah J. Dolman, Jacob Janey,
Facile preparation of α-amino ketones from oxidative ring-opening of aziridines by pyridine N-oxide
Facile preparation of α-amino ketones from oxidative ring-opening of aziridines by pyridine -oxide rg. Biomol. Chem., 2007, 5, 3428 Luo, Z.-B.; Wu, J.-Y.; ou, X.-L.; Dai, L.-X. Ts toluene Ts 80 o C John
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage
henium-catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage Kuninobu, Y.; Takata,.; Kawata, A.; Takai, K. rg. Lett. ASAP Et 5 6 cat. [ebr(c) 3 (thf)] 2 5 6 Current Literature
Total Synthesis of Callipeltoside A. Denmark Group Meeting Aaron Bailey September 23, 2008
Total Synthesis of Callipeltoside A Denmark Group eting Aaron Bailey September 23, 2008 Callipeltoside A First isolated from Lithistid sponge in 1996 Exhibits moderate cytotoxicity against human bronchopulmonary
Total synthesis of Spongistatin
Literature Semminar 1. Introduction: Total synthesis of Spongistatin Chen Zhihua (M2) Isolation: Pettit et al. J. rg. Chem. 1993, 58, 1302. Kitagawa et al. Tetrahedron Lett. 1993, 34, 1993. Fusetani et
JACS ASAP Article: Published 3/12/08. Lei Jiao, Changxia Yuan and Zhi-Xiang Yu. Current Literature: 3/29/08. David Arnold
Tandem h(i)-catalyzed [(5+2)+1] Cycloaddition/Aldol eaction for the Construction of Linear Triquinane Skeleton: Total Syntheses of (+)-irsutene and (+)-1- Desoxyhypnophilin JACS ASAP Article: Published
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols
A Tandem Semipinacol Rearrangement/Alkylation of a-epoxy Alcohols: An Efficient and Stereoselective Approach to Multifunctional 1,3-Diols B() 2 H H B() 2 H H Hu, X.-D.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.
Organic Tutorials 3 rd Year Michaelmas Transition Metals in Organic Synthesis: (General paper level) ! 1! Reading
rganic Tutorials 3 rd Year Michaelmas 2010 Transition Metals in rganic Synthesis: (General paper level) Reading 1. Lecture Course, and suggested references from this. 2. Clayden, Greaves, Warren and Wothers.
CEM 852 Final Exam. May 5, 2011
CEM 852 Final Exam May 5, 2011 This exam consists of 8 pages. Please make certain that your exam has all of the necessary pages. Total points possible for this exam are 150. In answering your questions,
Hirsutene and Δ 9(12) Capnellene. D. P. Curran (1986) Presenter: Mehdi Moemeni
irsutene and Δ 9(12) Capnellene D. P. Curran (1986) Presenter: Mehdi Moemeni Back Ground of Radical Structure In a modern context the first organic free radical identified was triphenylmethyl radical.
Synthesis of the Stenine Ring System from Pyrrole
Current Literature Presentation gor psenica 06/18/2011 Synthesis of the Stenine Ring System from Pyrrole Bates, R. W.; Sridhar, S. J. rg. Chem., 2011, 76, 5026 5035 gor psenica @ Wipf Group Page 1 of 16
transmetallate displace ox. add. M + (insert) (β-elim.)
Chapter IV. Transition Metal σ-alkyl Complexes I. General For much of the rest of this course it will be necessary to understand how σ-alkyl metal complexes are formed and how they react. This is summarized
TMSCl imidazole DMF. Ph Ph OTMS. Michael reaction. Michael reaction Ph R 3. epoxidation O R
eaction using diarylprolinol silyl ether derivatives as catalyst 1) C Et K C 3, ) MgBr, TF TMS hexane, 0 o C TBS p- C 6 4, T C Et 85%, 99% ee Angew. Chem., nt. Ed., 44, 41 (005). rg. Synth., 017, 94, 5.
Strategies for Stereocontrolled Synthesis
Chemistry. Synthetic rganic Chemistry II Lecture 3 March, 2007 Rick L. Danheiser Massachusetts Institute of Technology! Thermodynamic Control Strategies! Kinetic Control Strategies! Strategies for the
James D. White. A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab. Education Experience
A very productive professor 64 students graduated from his lab 94 postdocs have worked in his lab Education Experience Fraser Fleming University of Drexel Pavel agory University of Michigan Cambridge University,
BURIED TREASURES: CASCADES WE HAVEN'T SEEN
BURIED TREASURES: CASCADES WE AVE'T SEE Me Me Me 2 3 C C 3 3 C C 3 C 2 Me R. Robinson, J. Chem. Soc., 1917, 762 Cascades Articulated Main Entry: 1cas cade Pronunciation: (")kas-'kad Function: noun Etymology:
Total Synthesis of Rapamycin
. sman, CEM 20 //2007 Total ynthesis of Rapamycin Matthew L. Maddess, Miles. Tackett, idenori Watanabe, Paul E. ennan, Christopher D. pilling, James. cott, David P. sborn, and teven V. Ley* Angew. Chem.
VI. Metal alkyls from oxidative addition / insertion
V. Metal alkyls from oxidative addition / insertion A. Carbonylation - C insertion very facile, metal acyls easily cleaved, all substrates which undergo oxidative addition can in principle be carbonylated.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis
Development of Chiral Phosphine Olefin Ligands and Their Use in Asymmetric Catalysis
Development of Chiral osphine lefin Ligands and Their Use in Asymmetric Catalysis 2 Wei-Liang Duan July 31, 2007 Research Works in Hayashi Group, Kyoto University (ct, 2003 Mar, 2007) Conventional Chiral
Suggested solutions for Chapter 40
s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig
Ladderanes: Uses and Synthesis. Nicholas Anderson Denmark Group Meeting October 28, 2008
Ladderanes: Uses and Synthesis icholas Anderson Denmark Group Meeting ctober 28, 2008 utline Ladderane types and classifications Potential applications of ladderanes Synthesis of ladderanes Ladderane natural
Asymmetric Nucleophilic Catalysis
Asymmetric ucleophilic Catalysis Chiral catalyst X 2 Chiral catalyst X = alkyl, X 1 2 1 Vedejs, E.; Daugulis,. J. Am. Chem. Soc. 2003, 125, 4166-4173 Shaw, S. A.; Aleman,.; Vedejs, E. J. Am. Chem. Soc.
Chiral Proton Catalysis in Organic Synthesis. Samantha M. Frawley Organic Seminar September 14 th, 2005
Chiral Proton Catalysis in rganic Synthesis Samantha M. Frawley rganic Seminar September 14 th, 2005 Seminar utline Introduction Lewis Acid-assisted Chiral Brønsted Acids Enantioselective protonation for
JACS 1982: A Survey of Papers with a Focus on Synthetic Organic Chemistry
JAC 1982: A urvey of Papers with a Focus on ynthetic rganic Chemistry Baran Lab Group eting 15 ctober 2003 Carlos A. Guerrero eagents and thods 1 2 [] 2 2 1 1 PhC, Et 3 2 [] 2 1 2 1 By 1982, the [3 + 2]
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/ *&%&*,$.&-!"!3$!4$!5)01+!.*!06'2
!"#$%&&'!&(!)*+,-./!01"2.3$*4!"!#$!%$!%&'(') *+,!-$!%&'(').!'/012 546*&%&*,$.&-!"!3$!4$!5)01+!.*!06'2 C-C Bond Formation: Cross-coupling Reaction of rganometal Compounds with rganic alids M C-m + X-C C-C
Synthesis of the Tetrahydroisoquinoline Alkaloid (±)-Renieramycin G and a (±)-Lemonomycinone Analogue from a Common Intermediate
Synthesis of the Tetrahydroisoquinoline Alkaloid (±)-Renieramycin G and a (±)-Lemonomycinone Analogue from a Common Intermediate Philip Magnus* and Kenneth S. Matthews Department of Chemistry and Biochemistry,
Journal Club. Nick Tappin Renaud Group 21 May 2015
Journal Club Nick Tappin Renaud Group 21 May 2015 Total Synthesis of the AnAmitoAc Marine Macrolide ( )- Leiodermatolide ACE 2014, 53, 2692 2695 an Paterson*, K. K.- H. Ng, S. Williams, D. C. Millican,