The Legends of the Star Tetrodotoxin
|
|
|
- Rudolph Marshall
- 5 years ago
- Views:
Transcription
1 The Legends of the Star Tetrodotoxin Advisors: Prof. YANG Prof. CHEN Prof. TANG Reporter: Haixin YU
2 History Puffer Fish Delicious food in Japan fugu Poisonous For Japanese and Egyptians Millennia For Europeans 1727 A History of Japan Published by Dutch physician Englebert Kaempfer 2
![History Having no suspicion of its being of a poisonous nature, we ordered [the fish]to be dressed for supper; but very luckily, the operation of drawing and describing took up so much time that it](/docs-images/88/115624605/images/3-0.jpg "was too late, so that only the liver and row were dressed, of which [we] did but taste.")
3 History Having no suspicion of its being of a poisonous nature, we ordered [the fish]to be dressed for supper; but very luckily, the operation of drawing and describing took up so much time that it was too late, so that only the liver and row were dressed, of which [we] did but taste. About three o clock in the morning, we found ourselves seized with an extraordinary weakness and numbness all over our limbs. I had almost lost the sense of feeling; nor could I distinguish between light and heavy bodies of such as I had strength to move, a quart pot, full of water, and a feather being the same in my hand. A Voyage Toward the South Pole and Around the World Captain James Cook 3
4 Isolation Late 1800s Japanese Scientists 1911 by Dr. Tahara Armorphous Solid and Named Tetrodotoxin 1950 by Dr. Yokoo, Dr. Tsuda and Dr. Kawamura a crystaline Pure Tetrodotoxin Biosynthesizes by Bacterium By Pseudomonas. sp 4
5 Structure rd IUPAC Symposium on the Chemistry of Nature Products (Kyoto, Japan) Identified the structure, by Dr. Tsuda, by Dr. Goto, by Dr. Woodward, by Dr. Mosher Named Tarichatoxin which was isolated from California salamander 1970 Absolute Stereochemistry by X-ray Crystallographic Analysis by Dr. Furusaki 5
6 Structure Zwitterionic Architeture Compact 11 C Structrue 8 Oxygen Atoms 3 Nitrogen Atoms 9 Stereogenic Centers Dioxoadamantane Core Ortho Ester Functionality A Cyclic Guanidine Fully Subsituted Cyclohexane 6
7 Pharmacological effects Depending on the Dose Mild numbness Paralysis Coma Respiratory Failure Death Selective Inhibitor of Voltage- Gate Sodium Ion Channel Bioactivity 7
8 Bioactivity 8
9 Bioactivity 9
10 Total Synthesis Kishi Racemic JACS Isobe 2 Asymmetric JACS Angew Identified the structure Du Bois Asymmetric JACS Ken-ichi Sato 1 Racemic 1 Asymmetric 2 JOC 10
11 Retrosynthetic Analysis by Kishi 11
12 Retrosynthetic Analysis by Kishi 12
13 Synthetic Route by Kishi 13
14 Synthetic Route by Kishi 14
15 Synthetic Route by Kishi 15
16 Total Synthesis Kishi Racemic JACS Isobe 2 Asymmetric JACS Angew Identified the structure Du Bois Asymmetric JACS Ken-ichi Sato 1 Racemic 1 Asymmetric 2 JOC 16
17 Retrosynthetic Analysis by Du Bois 17
18 Retrosynthetic Analysis by Du Bois 18
19 Synthetic Route by Du Bois 19
20 Synthetic Route by Du Bois 20
21 Synthetic Route by Du Bois 21
22 Synthetic Route by Du Bois 22
23 Total Synthesis Kishi Racemic JACS Isobe 2 Asymmetric JACS Angew Identified the structure Du Bois Asymmetric JACS Ken-ichi Sato 1 Racemic 1 Asymmetric 2 JOC 23
24 Retrosynthetic Analysis by Isobe 24
25 Retrosynthetic Analysis by Isobe 25
26 Synthetic Route by Isobe 26
27 Synthetic Route by Isobe 27
28 Synthetic Route by Isobe 28
29 Comparisons and Contrasts Chemist Kishi Isobe Du Bois Type Racemic Asymmetric Asymmetric Highlights Diels-Alder synthesis of skeleton; 6 chiral centers established on cyclohexane core ring; Only ketal and acetyl protecting groups; Common reagents employed to carry out elegant chemistry. Diels-Alder reaction; Overman rearrangement; Intramolecular epoxide opening. Optimized the first Asymmetric total synthesis in 67 steps, 1.22% yield. Rhodium-catalyzed carbene and nitrene C-H insertions; Ph 2 Se 2 -promoted allylic oxidation; Shows power of organometallic chemistry in total synthesis Steps Yield 0.66% 0.25% 0.49% 29
30 Summary 30
31 References Isobe synthesis: Isobe, M., et. al. J. Am. Chem. Soc. 2003, 125, Overman Rearrangement: Overman, L. E. Acc. Chem. Res. 1980, 13, Sonogashira Coupling: Sonogashira, K., et. al. Tetrahedron Lett. 1975, 16, α-hydroxyl Lactone: Corey, E. J.; Ghosh, A. K. Tetrahedron Lett. 1988, 26, Structure: Woodward, R. B. Pure. Appl. Chem. 1964, 9, Tsuda, K., et. al. Chem. Pharm. Bull. 1964, 12, Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron 1965, 21, Absolute stereochemistry: Furusaki, A., et. al. Bull. Chem. Soc. Jpn. 1970, 43, Bioorganic studies: Narahashi, T.; Moore, J. W.; Scott, W. R. J. Gen. Physiol. 1964, 47, Hucho, F. Angew. Chem, Int. Ed. Engl. 1995, 34, Numa, S.; Noda, M. Ann. N.Y. Acad. Sci. 1986, 479, Other analog syntheses: Nishikawa, T., et. al. Angew. Chem., Int. Ed. 1999, 38, Asai, M., et. al. Tetrahedron 2001, 57, Nishikawa, T., et. al. J. Am. Chem. Soc. 2002, 124, Du Bois Synthesis: Hinman, A.; Du Bois, J., J. Am. Chem. Soc. 2003, 125, Rh-carbene C-H insertion: Espino, C. G.; Du Bois, J. Angew. Chem., Int. Rd. Engl. 2001, 40, Rh-nitrene C-H insertion: Guthikonda, K.; Du Bois, J., J. Am. Chem. Soc. 2002, 124, Ph 2 Se2 allylic oxidation: Barton, D. H. R.; Crich, D. Tetrahedron 1985, 41,
32 Acknowledgements Thank Everyone Here! 32
Total syntheses of 11-deoxytetrodotoxin and 8,11-dideoxytetrodotoxin*
Pure Appl. Chem., Vol. 75, Nos. 2 3, pp. 251 257, 2003. 2003 IUPAC Total syntheses of 11-deoxytetrodotoxin and 8,11-dideoxytetrodotoxin* Toshio Nishikawa, Daisuke Urabe, Kazumasa Yoshida, Tomoko Iwabuchi,
A Simple Introduction of the Mizoroki-Heck Reaction
A Simple Introduction of the Mizoroki-Heck Reaction Reporter: Supervisor: Zhe Niu Prof. Yang Prof. Chen Prof. Tang 2016/2/3 Content Introduction Intermolecular Mizoroki-Heck Reaction Intramolecular Mizoroki-Heck
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015 New strategies in organic synthesis nsf-cchf.com What
Total Synthesis of (+)-Gelsemine. Xuan Dong group seminar 12/19/2012
Total Synthesis of (+)-Gelsemine Xuan Dong group seminar 12/19/2012 Historical Background of Gelsemine First detected the presence of alk aloids in extracts of G. sempervir ens in 1870 by Wormley. 1876,
Rhodium Catalyzed Alkyl C-H Insertion Reactions
Rhodium Catalyzed Alkyl C-H Insertion Reactions Rh Rh Jeff Kallemeyn 5/17/05 1. Cyclopropanation The Versatile and Reactive Rhodium Carbene R + Et Rh 2 (Ac) 4 R C 2 Et N 2 2. [2,3] sigmatropic rearrangement
Palladium-Catalyzed Oxygenation of Unactivated sp 3 C-H Bonds
Palladium-Catalyzed xygenation of Unactivated sp 3 C- Bonds Pd(Ac) 2 5 mol% PhI(Ac) 2 1.1 eq. Pd 2 Ac Desai, L. P.; ull, K. L.; Sanford *, M. S. University of Michigan J. Am. Chem. Soc. 2004, 126, ASAP
Total Synthesis of (+)-Cytosporolide A via a Biomimetic
Literature report Total Synthesis of (+)-Cytosporolide A via a Biomimetic etero-diels Alder Reaction Reporter: Zhang-Pei Chen Checker: Shu-Bo u Date: 29/12/2015 Takao, K. et al. Takao, K. et al. J. Am.
II. Special Topics IIA. Enolate Chemistry & the Aldol Reaction
P. Wipf - Chem 2320 1 3/20/2006 II. Special Topics IIA. Enolate Chemistry & the Aldol Reaction Boger Notes: p. 147-206 (Chapter VIII) Carey/Sundberg: B p. 57-95 (Chapter B 2.1) Problem of the Day: Wang,
Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds*
Pure Appl. Chem., Vol. 72, No. 9, pp. 1715 1719, 2000. 2000 IUPAC Titanacyclopropanes as versatile intermediates for carbon carbon bond formation in reactions with unsaturated compounds* O. G. Kulinkovich
Nitrogen Centered Radical Ligands Nagashima Nozomu
1 Nitrogen Centered Radical Ligands 2015. 7. 4. Nagashima Nozomu 1. Introduction 2 3 Aminyl radical 1) D. E. Wiliams, JACS, 1966, 88, 5665 2) Y. Teki et al. JOC, 2000, 65, 7889 Sterically protected aminyl
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,
Converting Cycloalkanones into N- Heterocycles: Formal Synthesis of ( )-Gephyrotoxin 287C. Claude Spino et al., J. Org. Chem. 2013, 78,
Converting Cycloalkanones into N- Heterocycles: Formal Synthesis of ( )-Gephyrotoxin 287C Claude Spino et al., J. Org. Chem. 2013, 78, 12532 12544. Poison frog alkaloids Isolated from poison frog skin.
Suggested solutions for Chapter 32
s for Chapter 32 32 PBLEM 1 Explain how the stereo- and regio- chemistry of these reactions are controlled. Why is the epoxidation only moderately diastereoselective, and why does the amine attack where
Some questions and answers that we will get out of this example synthesis:
UTLINE 535 LECTURE 3 (2004) Page 22 The Synthesis of Cubane I am showing you this synthesis because it is elegant and exemplifies many different concepts. We can use it to talk in context about the philosophical
(+)-Saxitoxin : A First and Second Generation Stereoselective Synthesis
(+)-Saxitoxin : A First and Second Generation Stereoselective Synthesis Fleming, J. J.; McReynolds, M. D.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 9964. Literature Presentation Zhenjie Lu Sep 28, 2007
I. Introduction. II. Retrosynthetic Analysis. Andrew Baggett. Liu lab
Total Synthesis of Limonin Shuji Yamashita,* Akito Naruko, Yuki Nakazawa, Le Zhao, Yujiro Hayashi, Masahiro Hirama Tohoku University, Department of Chemistry, Aramaki-aza aoba, Aoba-ku, Sendai 980-8578
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction. Eric Gillis 4/19/07
The synthesis of molecules containing quaternary stereogenic centers via the intramolecular asymmetric Heck reaction Eric Gillis 4/19/07 Quaternary stereocenters in complex small molecules Retrosynthetic
The Story of Azadirachtin. Weiwu Ren
The Story of Azadirachtin Weiwu Ren 2015-12-17 Content 1 Introduction 2 Isolation and Structure Determination 3 Synthetic Study towards Azadirachtin 4 Total Synthesis of Azadirachtin Ley s Work Watanabe
Synthesis of Abyssomicin C. Marie-Caroline Cordonnier Litterature Review 23/01/2009
Synthesis of Abyssomicin C Marie-Caroline Cordonnier Litterature Review 23/01/2009 Isolation Isolated in 2004 from the actinomycete Verrucosispora strain collected from a sediment at a depth of 289m in
Organocatalytic Umpolung via N- Heterocyclic Carbenes. Qinghe Liu Hu Group Meeting August 20 th 2015
rganocatalytic Umpolung via N- Heterocyclic Carbenes Qinghe Liu Hu Group Meeting August 20 th 2015 Contents Part 1: Introduction Part 2: N-Heterocyclic carbene-catalyzed umpolung: classical umpolung, conjugated
Metalloporphyrin. ~as efficient Lewis acid catalysts with a unique reaction-field~ and. ~Synthetic study toward complex metalloporphyrins~
Metalloporphyrin ~as efficient Lewis acid catalysts with a unique reaction-field~ and ~Synthetic study toward complex metalloporphyrins~ Literature Seminar Kenta Saito (D1) 1 Topics Chapter 1 ~as efficient
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry.
Research in our group encompasses the following 4 areas in Synthetic Organic Chemistry. 1] Development of Asymmetric Catalysis 2] Total Synthesis of Natural products 3] Development of Novel Protecting-Group-Free
Iron in the Service of Chromium: The ortho-benzannulation of trans,trans-dienyl Fischer Carbene Complexes
Iron in the Service of Chromium: The ortho-benzannulation of trans,trans-dienyl Fischer Carbene Complexes Yiqian Lian and William D. Wulff (Michigan State University) JACS 2005, 127, 17162-17163. Markus
Some questions and answers that we will get out of this example synthesis:
UTLINE CE535 SESSIN 3 (2007) Page 24 The Synthesis of Cubane I am showing you this synthesis because it is elegant and exemplifies many different concepts. We can use it to talk in context about the philosophical
N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations
Angew. Chem. Int. Ed. 2017, 10.1002. 1 N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Enantioselective Remote Functionalizations Reporter: En Li Supervisor: Prof. Yong
Recent Developments in the Chemistry of Polyvalent Iodine Compounds
Recent Developments in the Chemistry of Polyvalent Iodine Compounds Jiang Zhongping 2005-9-23 Content I. Introduction II. Iodine(III) Compounds III. Iodine(V) Compounds IV. Conclusions Introduction Why
Advanced Organic Chemistry
D. A. Evans, G. Lalic Question of the day: Chemistry 530A TBS Me 2 C Me toluene, 130 C 70% TBS C 2 Me H H Advanced rganic Chemistry Me Lecture 16 Cycloaddition Reactions Diels _ Alder Reaction Photochemical
Chemistry 610: Organic Reactions Fall 2017
Instructor Prof. David Powers Office: Chemistry 320 Phone: 979.862.3089 E-mail: david.powers@chem.tamu.edu Learning Outcomes Chemistry 610: Organic Reactions Fall 2017 Tuesday and Thursday 2:20 3:35 PM
Total Synthesis of Maoecrystal V: Early-Stage of C-H Functionalization and Lactone
Literature Report Total Synthesis of Maoecrystal V: arly-stage of C- Functionalization and Lactone Assembly by Radical Cyclization Reporter: Ji Yue Checker: Chen Muwang Date: 2013/12/02 Zakarian, A. et
Chapter 11 Outline: Ethers, Epoxides & Sulfides
Chapter 11 Outline: Ethers, Epoxides & Sulfides Review Nomenclature & Physical Properties on your own 1. Structure of Ethers & Epoxides 2. Preparation of Ethers & Thioethers 3. Reactions of Ethers 4. Preparation
Use of the non-aldol aldol process in the synthesis of the C1 C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans
Pergamon Tetrahedron Letters 41 (2000) 9719 9723 TETRAHEDRON LETTERS Use of the non-aldol aldol process in the synthesis of the C1 C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans
Rising Novel Organic Synthesis
Literature report Rising Novel Organic Synthesis Methods Based on the Cleavage of N-N and N-O Bonds Reporter: Zhang-Pei Chen Checker : Mu-Wang Chen Date: 04/03/2014 Kürti, L. et al. Kürti, L. et al. Science
ORGANIC - CLUTCH CH ALCOHOLS, ETHERS, EPOXIDES AND THIOLS
!! www.clutchprep.com CONCEPT: ALCOHOL NOMENCLATURE Glycols: Alcohols with two hydroxyls are called ; with three hydroxyls are called Always give most priority to the OH group. EXAMPLE: Provide the correct
Total Synthesis of Saxitoxin
Total ynthesis of axitoxin 2 2 2 John Baird April 11, 2006 1 First isolated in 1957 by chantz et al Isolation and Properties X-Ray tructure obtained in 1975 Freely soluble in water and methanol ptical
Literature Report 2. Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids. Date :
Literature Report 2 Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids Reporter : Zhou-Hao Zhu Checker : Xiao-Yong Zhai Date : 2018-04-23 Liu, Y.-T.; Li, L.-P.; Xie, J.-H.*; Zhou, Q.-L. Angew.
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
Functionalized main-group organometallics for organic synthesis*
Pure Appl. Chem., Vol. 74, No. 1, pp. 11 17, 2002. 2002 IUPAC Functionalized main-group organometallics for organic synthesis* Paul Knochel, Eike Hupe, Wolfgang Dohle, David M. Lindsay, Véronique Bonnet,
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity
Planar-Chiral Phosphine-Olefin Ligands Exploiting a (Cyclopentadienyl)manganese(I) Scaffold to Achieve High Robustness and High Enantioselectivity Reporter: Cong Liu Checker: Hong-Qiang Shen Date: 2017/02/27
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo 2014.1.6 1 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook
Palladium-catalyzed sp 3 C H activation. Yan Xu Dong Group Meeting Apr. 2, 2014
Palladium-catalyzed sp 3 C H activation, Yan Xu Dong Group Meeting Apr. 2, 2014 Content 1 Allylic C H activation 2 Benzylic C H activation Palladiumcatalyzed sp 3 C H activation 3 4 Common sp 3 C H activation:
Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates
Pure & Appl. Chern., Vol. 70, No. 5, pp. 11 17-1 122, 1998. Printed in Great Britain. (0 1998 IUPAC Metal-catalyzed asymmetric hetero-diels-alder reactions of unactivated dienes with glyoxylates Mogens
Page 1 of 9. Sessional Examination (November 2017) Max Marks: 20 Date: Time: One Hour. Model Answers
Page 1 of 9 Sessional Examination (November 2017) Class: B. Pharm-II yr (III sem) Subject: Pharma Org. Chem-II Max Marks: 20 Date: 14.11.2017 Time: One Hour Model Answers Q. 1. Solve the following (ANY
Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
Pure Appl. Chem., Vol. 76, No. 3, pp. 651 656, 2004. 2004 IUPAC Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
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,
KOT 222 Organic Chemistry II
KOT 222 Organic Chemistry II Course Objectives: 1) To introduce the chemistry of alcohols and ethers. 2) To study the chemistry of functional groups. 3) To learn the chemistry of aromatic compounds and
Chemistry 432 Lecture Notes Updated: Spring Nucleophiles and Electrophiles: The Basis of Organic Chemistry
Chemistry 432 Lecture Notes Updated: Spring 2016 Course Organization: Things You Need to Know 1. Named Reactions and Reagents 2. Vocabulary 3. Concepts 4. HOW TO DO SYNTHESIS Nucleophiles and Electrophiles:
-catalyzed reactions utilizing isocyanides as a C 1
Pure Appl. Chem., Vol. 78, No. 2, pp. 275 280, 2006. doi:10.1351/pac200678020275 2006 IUPAC GaCl 3 -catalyzed reactions utilizing isocyanides as a C 1 source* Mamoru Tobisu, Masayuki Oshita, Sachiko Yoshioka,
Reporter: Yue Ji. Date: 2016/12/26
Literature Report (11) Total Synthesis of Rubriflordilactone B Reporter: Yue Ji Checker: Mu-Wang Chen Date: 2016/12/26 Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A.* Angew. Chem. Int. Ed. 2016, 55, 6964. Laboratory
Glyoxylic acid derivatives in asymmetric synthesis*
Pure Appl. Chem., Vol. 72, No. 9, pp. 1589 1596, 2000. 2000 IUPAC Glyoxylic acid derivatives in asymmetric synthesis* Janusz Jurczak 1,2 and Tomasz Bauer 1 1 Department of Chemistry, University of Warsaw,
Suggested solutions for Chapter 41
s for Chapter 41 41 PBLEM 1 Explain how this synthesis of amino acids, starting with natural proline, works. Explain the stereoselectivity of each step after the first. C 2 C 2 3 CF 3 C 2 2 Pd 2 C 2 +
Rhodium Catalyzed Hydroacylation
Literature Report Changbin Yu 2012-12-04 检查 : 蔡先锋 Rhodium Catalyzed ydroacylation Vy M. Dong* Education h.d. California Institute of Technology, 2004 M.S. University of California at Berkeley, 2000 BS
Asymmetric Palladium Catalyzed Cross-Coupling Reactions. Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1
Asymmetric Palladium Catalyzed Cross-Coupling Reactions Topic Talk September 4 th, 2014 Morken Lab Emma Edelstein 1 Palladium Catalyzed Cross-Coupling Reactions 2 Kumada/Negishi Cross-Coupling Kumada:
Ahmad Masarwa Selective Metal-Mediated C-C Bond Activation of Strain Compounds: Application to Challenging non-natural Product Synthesis
Ahmad Masarwa Selective Metal-Mediated C-C Bond Activation of Strain Compounds: Application to Challenging non-natural Product Synthesis For the last few decades, organic chemists have spent much effort
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
Nucleophilic Heterocyclic Carbene Catalysis. Nathan Werner Denmark Group Meeting September 22 th, 2009
Nucleophilic Heterocyclic Carbene Catalysis Nathan Werner Denmark Group Meeting September 22 th, 2009 Thiamine Thiamine Vitamin B 1 The first water-soluble vitamin described Is naturally synthesized by
Overview of Synthesizing Merrilactone A
verview of Synthesizing Merrilactone A = Contents = I. Beginning II. Danishefsky's Route III. irama & Inoue's Route IV. Frontier's Route V. Conclusion 6th / Feb./ 2008 Literature Seminar ~ B4 part ~ Takafumi
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
Cambrian Explosion, Complex Eukaryotic Organism, Ozonosphere 3
Reporter: Wang Yuefan Reporter: Wang Yuefan Supervisor: Prof. Yang Zhen Supervisor: Prof. Yang Zhen Prof. Chen Jiahua Prof. Chen Jiahua 1 2011-12-2727 2011-02 2012-03 02-25 03-23 25 Content Preface Nature
Chiral Ru/PNNP complexes in catalytic and stoichiometric electrophilic O- and F-atom transfer to 1,3-dicarbonyl compounds*
Pure Appl. Chem., Vol. 78, No. 2, pp. 391 396, 2006. doi:10.1351/pac200678020391 2006 IUPAC Chiral Ru/PNNP complexes in catalytic and stoichiometric electrophilic O- and F-atom transfer to 1,3-dicarbonyl
PART I: CARBENES and NITRENES
ACS Group eting Problem Session Feb/Mar 2009 Mahesh Mohan Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ Reactive Intermediates in rganic Synthesis PART I: CARBEES
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction
Story Behind the Well-Developed Chiral Lewis Acid in Asymmetric Diels-Alder reaction Reporter: Zhang Sulei Supervisors: Prof. Yang Zhen Prof. Chen Jiahua Prof. Tang Yefeng 2015-10-05 1 Contents Background
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY
STEREOELECTRONIC EFFECTS (S.E.) IN ORGANIC CHEMISTRY Pierre Deslongchamps (version du 16 février 2010) Cf. pour le livre: http://pages.usherbrooke.ca/pdeslongchamps/cv.htm 1 SECTION 8 Stereoelectronic
sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito
1 sp 3 C-H insertion by α-oxo Gold Carbene B4 Kei Ito 2016. 1. 30 1. Introduction 2 About Carbene 3 Brief history of carbene (~2000) Carbene Neutral compounds featuring a divalent carbon atom with only
Organic Cumulative Exam October 13, 2016
rganic Cumulative Exam ctober 3, 206 Answer only three of the five questions. o more than three question answers will be graded and any work not to be considered must be clearly marked as such. Clearly
FORBIDDEN 1,2-CARBANION SHIFTS MECHANISM AND APPLICATION OF THE FRITSCH- BUTTENBERG-WIECHELL REARRANGEMENT. Chun Ho Lam
1 FORBIDDEN 1,2-CARBANION SHIFTS MECHANISM AND APPLICATION OF THE FRITSCH- BUTTENBERG-WIECHELL REARRANGEMENT Chun Ho Lam 17 th November 2010 Chun Ho Lam 17 th November, 2010 Contents 2 Section 1: Discovery
Catalytic Asymmetric Total Syntheses of Quinine and Quinidine
Catalytic Asymmetric Total Syntheses of Quinine and Quinidine 8 7 9 2 1 3 4 6 5 7 9 8 2 1 3 4 6 5 Quinine Zhensheng Ding Quinidine January 22 2004 Chinese ew Year Day 1. Jacobsen, E.,. J. Am. Chem. Soc.
1. WORK PROGRESS AND ACHIEVEMENTS DURING THE PERIOD. A summary of progress towards objectives and details for each task;
1. WORK PROGRESS AND ACHIEVEMENTS DURING THE PERIOD A summary of progress towards objectives and details for each task; In Nature, a vast array of complex biomolecules, including peptides, oligonucleotides,
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.
C H Activated Trifluoromethylation
Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation
Name: Student No: CHEM Prof. Marks) (100
Name: Student No: Page 1 of 14 CEM 2220 Organic Chemistry II: Reactivity and Synthesis Prof. P.G. ultin, Dr.. Luong FINAL EXAM Winter Session 2012R Friday April 20, 20122 1:30 pm 4:30 pm Frank Kennedy
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
The Total Synthesis of Vitamin B12
The Total Synthesis of Vitamin B12 The most advanced synthetic intermediate as of 1968 Nathan S. Werner Denmark Group Meeting September 28 th, 2010 Biology of Vitamin B 12 Vitamin B 12, common name cobalamin,
Review. Frank Glorius & His Rh(III) C-H Activation. Li Yuanhe. Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21
Review Frank Glorius & His Rh(III) C-H Activation Li Yuanhe Supervisors: Prof. Yang Prof. Chen Prof. Tang Prof. Luo 1 /21 Author Introduction Prof. Dr. Frank Glorius 1972 Born 1991-1992 Military service
Suggested solutions for Chapter 34
s for Chapter 34 34 PRBLEM 1 Predict the structure of the product of this Diels- Alder reaction. C 2 +? 3 Si Can you deal with a moderately complicated Diels- Alder? The diene is electron- rich and will
Copper-mediated asymmetric transformations*
Pure Appl. Chem., Vol. 74, No. 1, pp. 37 42, 2002. 2002 IUPAC Copper-mediated asymmetric transformations* Alexandre Alexakis Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet,
Alkyne Dicobalt Complexes in Organic Chemistry
Alkyne Dicobalt Complexes in Organic Chemistry Sun Baochuan Supervisors: Prof. Yang Prof. Chen Prof. Tang Cobalt - Co From German word kobald - evil spirits Atomic Number: 27 Group: 9 Period: 4 3d 7 4s
Asymmetric Catalysis by Lewis Acids and Amines
Asymmetric Catalysis by Lewis Acids and Amines Asymmetric Lewis acid catalysis - Chiral (bisooxazoline) copper (II) complexes - Monodentate Lewis acids: the formyl -bond Amine catalysed reactions Asymmetric
CEM 351 2nd EXAM/Version A Friday, October 17, :50 2:40 p.m. Room 138, Chemistry
Name (print) Signature Student # Section Number CEM 351 2nd EXAM/Version A Friday, October 17, 2003 1:50 2:40 p.m. Room 138, Chemistry Ann Swerkey Grade? 1.(20 2.(20. 3.(20 4.(20 5.(20 6.(20 TOTAL 100
KJM 3200 Required Reading (Pensum), Fall 2016
KJM 3200 Required Reading (Pensum), Fall 2016 John McMurry: Organic Chemistry 8 nd ed. or Paula Y. Bruice, Organic Chemistry 7 nd ed. as specified below, as specified below. Lise-Lotte Gundersen KJM 3200.
Synthetic Organic Chemistry Final Exam (6KM33) Tuesday, 8th April, 2014, 9:00 12:00 (3 h)
Synthetic rganic Chemistry Final Exam (6KM33) Tuesday, 8th April, 2014, 9:00 12:00 (3 h) This is an open-book written exam. The course textbooks (Warren & Wyatt, 2 nd Ed.) with personal notes and worked
Dr. P. Wipf Chem /10/2007
I. Basic Principles I-N. Epoxides 1. High-Valent TM(d0) Epoxidations Mo, V, W (H 2 WO 4 ), Ti, Al serve as catalysts with t-buo 2 H or other peroxides as stoichiometric oxidants. Toluene is a frequent
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)
UNIVERSITY OF VICTORIA PRACTICE FINAL EXAMINATION APRIL 2017
UNIVERSITY OF VICTORIA PRACTICE FINAL EXAMINATION APRIL 2017 CHEMISTRY 335: SYNTHETIC METHODS IN ORGANIC CHEMISTRY A01 CRN 20531 (PROF. JEREMY WULFF) Name: Student Number: Please display your student ID
Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang!
1! Domino Reactions in Total Synthesis! Reporter: Tianhe Yang! Supervisors: Prof. Yang! Prof. Chen! Prof. Tang! 2! utline! 1. Brief Introduction! 2. ucleophilic Dominoes! 3. Electrophilc Dominoes! 4. Radical
Career Review of Dean Toste I. 2015/9/9 Zhi Ren
Career Review of Dean Toste I 2015/9/9 Zhi Ren Introduction F. Dean Toste, now in UC Berkeley Career: Full Professor since 2009-now Associate Professor 2006-2009 Assistant Professor 2002-2006 Faculty Scientist
Total Synthesis of ( )-Nakadomarin A
Total Synthesis of ( )-Nakadomarin A Pavol Jakubec, Dane M. Cockfield, and Darren J. Dixon University of Oxford and University of Manchester, UK J. Am. Chem. Soc. 2009, ASAP DOI: 10.1021/ja908399s Marie-Céline
Luckily this intermediate has three saturated carbons between the carbonyls, which again points to a Michael reaction:
Retrosynthesis Practice Problems Answer Key October 1, 2013 1. Draw a retrosynthesis for how to make the compound shown below from starting materials with eight or fewer carbon atoms. The first step is
Recent Developments in Alkynylation
--New approaches to introduce an alkynyl group Reporter: Zhao-feng Wang Supervisor: Yong Huang 2013-03-27 Contents 1. Introduction of Acetylene Chemistry 2. Nucleophilic alkynylation : Classic text book
Selective sp 3 C-H Hydroxylation. Xin Zhang Department of Chemistry Michigan State University 11/10/2010
Selective sp 3 C-H Hydroxylation Xin Zhang Department of Chemistry Michigan State University 11/10/2010 Content Introduction Tertiary sp 3 C-H Hydroxylation Secondary sp 3 C-H Hydroxylation Primary sp
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
Steroids. Prostaglandins
Steroids Cholesterol Progesterone Cortisone PGF 1 C 2 C 2 Prostaglandins C 2 PGE 1 PGA 1 C 2 Six-membered Rings Five-membered Rings Stereocontrol in Cyclic Systems Acyclic Diastereoselection Biomimetic
Chemistry Final Examinations Summer 2006 answers
Chemistry 235 - Final Examinations Summer 2006 answers A GEERAL CEMISTRY answers are given from 1-20: no reaction C 3 CC 3 Ph C C C C C 3 Et 2 2 2 B. REACTIS AD REAGETS [32 MARKS] 2. A single substance
Mechanistic Studies of Allylsilane Rearrangement
chanistic Studies of Allylsilane Rearrangement Thesis: The goal of our project is to determine the operating mechanism in the transformation of α-siloxy allylsilanes to vinyl silanes. Elucidating the mechanism
Midterm Exam #1 /310 CHEM 6352 Fall 2012
Midterm Exam #1 /310 CEM 6352 Fall 2012 ( %) Name ct 5 th, 2012 18:30-21:00 You may NT use any references or aids to complete the following with the exception of a chemical model set and the scrap paper
Stereocontrolled organocatalytic synthesis of prostaglandin PGF 2 in seven steps
Stereocontrolled organocatalytic synthesis of prostaglandin PGF 2 in seven steps Graeme Coulthard, William Erb, Varinder K. Aggarwal Nature. August 15, 2012. DI: 10.1038/nature11411 N C 2 then [Bn 2 N
NOT TO BE REMOVED FROM THE EXAMINATION HALL
A copy of the Level III (FHEQ Level 6) Equation and Data Sheet booklet is provided. The use of hand-held, battery-operated, electronic calculators will be permitted subject to the regulations governing
Chapter 4 Functional Group Transformations: Oxidation and Reduction. 4.8 Terminology for Reduction of Carbonyl Compounds
Chapter 4 Functional Group Transformations: Oxidation and Reduction Oxidation states (numbers) Less E.N. than C = -1 More E.N. than C = +1 C = 0 H H H C C OH H H 4.8 Terminology for Reduction of Carbonyl
MODULE CODE: CHEM10003 ORGANIC CHEMISTRY 4 EXAM
School of Science and Sport Physical Sciences, Chemistry Paisley Campus Session 2014-15 Trimester 2 MDULE CDE: CHEM10003 RGANIC CHEMISTRY 4 EXAM Date: 15th May 2015 Time: 10.00am 12.00pm Attempt THREE
Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide
General Papers ARKIVC 2008 (xii) 103-108 Copper-catalyzed cleavage of benzyl ethers with diacetoxyiodobenzene and p-toluenesulfonamide Ling He a,b, Qin Wang a, Guo-Chuan Zhou b, Lei Guo b, and Xiao-Qi
Chapter 12: Carbonyl Compounds II
Chapter 12: Carbonyl Compounds II Learning bjectives: 1. Recognize and assign names to aldehydes and ketones. 2. Write the mechanism for nucleophilic addition and nucleophilic addition-elimination reactions