Total Synthesis towards Maoecrystal V
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1 Total Synthesis towards Maoecrystal V isolated from the leaves of a Chinese medicinal herb, Isodon eriocalyx in structure was determined by comprehensive NMR and MS spectroscopic analysis and confirmed by singlecrystal X-ray diffraction study. exhibits highly selective antitumor activity, ela cells with IC 50 = 60 nm (cis-platin: IC 50 = 0.99 µg/ml). belongs to the family of C 19 diterpenoid, specifically entkauranoids. Contain highly congested polycyclic core. 7 stereocenters, 3 of which are quaternary stereocenters. 1 total synthesis and 6 partial synthesis have been reported till now. rg. Lett., 2004, 6 (23), pp
2 EDUCATIN Ph. D. In Chemistry The Chinese University of ong Kong ( ) M.S. in dicinal Chemistry Shenyang College of Pharmacy, P. R. China ( ) B.S. in dicinal Chemistry Shenyang College of Pharmacy, P. R. China ( ) EXPERIENCE present present Changjiang Professor College of Chemistry, Peking University, Beijing, China Research Interest: Total Synthesis of Natural Product and rganometallic Chemistry Diversity riented Synthesis and Chemical Biology Director of Chemistry XTL Biophamaceutical, New York, USA Research Interest: dicinal Chemistry and Combinatorial Chemistry ,9 Co-Founder and Director of Chemistry VivoQuest. Inc. New York, USA Research Interest: Anti-Viral Drug Discovery Institute fellow arvard Institute of Chemistry and Cell Biology, arvard University Research Interest: Diversity riented Synthesis Yang Zhen, Ph.D. Changjiang Professor College of Chemistry Peking University, Beijing, China Assistant Professor The Scripps Research Institute Research Interest: Total Synthesis of Complex Natural Products Postdoctoral Fellow The Scripps Research Institute Topic: Total Syntheses of Taxol, Brevetoxin A and Epothilone A NRS AND AWARDS 2000 s Young Investigator Award (abroad), NSF of China 2001 s Glaxo-Simth-Kline Drug Discovery and Development Award (USA) 2004 s Young Investigator Award, NSF of China 2005 Eli Lilly Scientific Excellence Award (China) Research Interests: Development of synthetic methods for the synthesis of complex natural , 23 papers and 4 patents with Nicolaou Chuang-chuang Li, Ph.D. Associate Professor
3 Yang s Total Synthesis of Maoecrystal V Ac Wessely xidative dearomatization and sequential IMDA WE MM Et P Et N 2 MM - insertion P Et Et J. Am. Chem. Soc., 2010, 132 (47), pp steps, 2% overall yield
4 Yang s Total Synthesis of Maoecrystal V P Et Et N 2 MM Na, TF, 2. TFA, C 2 Cl 2, rt 90% P Et Et J. Am. Chem. Soc., 2010, 132 (47), pp % Rh 2 (Ac) 4, Ph, 60% MM EDCI, DMAP, C 2 Cl 2, rt 82% P Et Et 2. TsN 3, DBU, 0 C 81% 1. tbuk, (C)n, TF, 0 C 95% C 2 R 1 R 2 Ac MM Pb(Ac) 3 pyridine, CCl 3, 60 C MM 88% 6a (12%) 6b (72%) LiAl 4, TF, rt, LiAl 4, TF, rt 88% Ac Pb(Ac) 4, Ac, 0 C then Ph 145 C, 24 h 2a (28%) 2b (12%) 2c (36%) 2 C R1=, R2= R1=, R2= 2 C R 1 2a,b MM Cationic -interaction (Bu 4 N)B 4,, 40 C 65% (89% brsm) R 2 MM R1=, R2= Ac 2c Ac
5 Yang s Total Synthesis of Maoecrystal V Ac 1. NBS, (PhC 2 ) 2 CCl 4, reflux, 2 h 90% 2. Bu 3 Sn, TEMP Ph, reflux, 2 h 75% N Ac 1. Zn, Ac, TF, 2 70 C, 2 h 85% 2. SmI 2, TF, rt, 10 min 88% Lindlar cat., TF rt, 2 h 92% DBU, toluene, 100 C, 1 h 48% (90% brsm) DMP, C 2 Cl 2, rt, 1 h 88% J. Am. Chem. Soc., 2010, 132 (47), pp
6 Baran s Synthesis towards Maoecrystal V SiR 3 C + C rg. Lett., 2009, 11 (21),
7 Baran s Synthesis towards Maoecrystal V MM TBS TBS MM BiCl 2 dr = 7:3, 67% TFA 65%, DBU C TBS TBS MM 88% 1. Li(t-Bu) 3 Al, 72% 2. Cl Pb(Ac) 4, Ac dr = 7:3, 81% 69% TBS Ac Ac Ac 165 C BF 3 Et 2 79% TBS 82% Ac 2, Pd/C SmI 2 rg. Lett., 2009, 11 (21), % TBS dr = 17:3, 76% TBS
8 Nicolaou s Synthesis towards Maoecrystal V C 2 1. MM C 2 1. Na Br N MM Pd(TFA) 2, Ag 2 C 3 2. BBr 3 57% over 2 steps 2. Na 2 C 3, I 3. MMCl, Na 37% C 2 1. TBSTf, Et 3 N PIFA 2. K 2 C 3, hydroquinone then 1 N Cl 41% 83% Pd/C, 2 PIFA Chem. Commun., 2010, 46, Na 2. ClC 2 I, KtBu 18-crown-6 42% + 66% 33%
9 Danishefsky s Synthesis towards Maoecrystal V P P MM P TBS P Tetrahedron Letters 50 (47), 25, 2009,
10 Danishefsky s Synthesis towards Maoecrystal V tbu tbu P Br C 3 1. Pd(Ac) 2, K 3 P 4, TF 80 C, 12 h 91% 2. TMSCN 2, ünigʼs base C 3 CN/ = 9:1, 6 h 100% 1. Bu 3 SnC 2 MM, BuLi TF, -78 C to - 40 C 30 min, 0.5% Cl work-up 75% Stork-Danheiser protocol MM 1. Cl/, 50 C 75% 2. PivCl, Py, DCM, 12 h 96% Piv 1. NaB 4, CeCl 3, 0 C, 2 h 93% 2. MMCl, ünigʼs base DCM, 12 h 95% MM Piv 1. DIBAL-, -78 C DCM, 30 min 95% 2. K, 18-crown-6 IC 2 SnBu 3 0 C, TF, 6 h 90% Tetrahedron Letters 50 (47), 25, 2009, MM SnBu 3 n-buli, -78 C to -20 C TF, 6 h 88% Witting-Still rearrangement MM
11 Danishefsky s Synthesis towards Maoecrystal V MM Li, N 3 (l), t-bu/tf -78 C, 20 min, -33 C, 40 min MM 1 N Cl, 0 C TF/ (10:1), 8 h 2 steps, 78% MM!:" = 1:3!:" = 1:3 Cl C 2 1. Py, DCM, 0 C 72% 2. TBSTf, TEA DCM, 0 C, 15 h 81% MM TBS C C, sealed tube toluene, 12 h 2. TBAF, 0 C, TF 2 steps, 48% MM C 2 Wrong Facial Selectivity Tetrahedron Letters 50 (47), 25, 2009,
12 Trauner s Synthesis towards Maoecrystal V Reverse Prenylation Cyanohydrin formation Alkylation tathesis TBS rg. Lett., Article ASAP DI: /ol102446u
13 Trauner s Synthesis towards Maoecrystal V TBS LDA, C 2 1. DMP, 90% TBS -40 C, 92% pen book effect TBS 2. NaB 4, 92% TBS LDA, C 2-40 C 65% TBS 3, 2 S 46% TBS rg. Lett., Article ASAP DI: /ol102446u
14 Trauner s Synthesis towards Maoecrystal V TBS X rg. Lett., Article ASAP DI: /ol102446u
15 Trauner s Synthesis towards Maoecrystal V TBS TBS Et dr = 7:1 TMSA, BuLi 75% TMS TBS Et Na, 40 C 82% TBS 2, Pd/CaC 3, Pyr 96% TBS LDA, C 2-40 C to rt TBS 12% 54% TBS rg. Lett., Article ASAP DI: /ol102446u
16 Thomson s Synthesis towards Maoecrystal V Lots of FGIs P X P X DA P Nazarov P X rg. Lett., 2010, 12 (13),
17 Thomson s Synthesis towards Maoecrystal V 1. LDA/TMSCl, m-cpba TBS 1. Na, N TBS 2. TBSCl, Im 70% over 2 steps 2. Li 73 % over 2 steps FeCl 3 72% TBS Necessary for following DA 1. DIBAL N 44% over 2 steps TBS N 2 1. K 2. Pd/C, 2 3. Jones Rgt. 86% N 2 N 2 N 2 TBS TMSI/MDS m-cpba 88% TBS Baeyer-Villiger CF 3 C 52% Grob fragmentation PhI(Ac) 2 /I 2, hv TBS rg. Lett., 2010, 12 (13), %
18 Thomson s Synthesis towards Maoecrystal V N 2 N 2 TBS 1. K 2. Jones Rgt. TBS Pd/C, 2 TBS 3. TMSI/MDS m-cpba 75% 71% 5 I 6, TBS NaB 4 TBS rg. Lett., 2010, 12 (13),
Towards Maoecrystal V: A Comparison of Recent Strategies
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