Applications of chiral allenylzinc additions and Noyori asymmetric reductions to an enantioselective synthesis of a C3-C13 precursor of the polyketide phosphatase inhibitor cytostatin

被引:26
作者
Marshall, JA [1 ]
Ellis, K [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA
关键词
allenylzinc; asymmetric reduction; polyketide; hydrogenation;
D O I
10.1016/j.tetlet.2003.12.067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 12-step synthesis of a C3-C13 precursor of the protein phosphatase inhibitor cytostatin is described. Key stereocenters were introduced by a chiral allenylzinc addition and Noyori asymmetric-transfer hydrogenation. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1351 / 1353
页数:3
相关论文
共 14 条
[1]   CYTOSTATIN, A NOVEL INHIBITOR OF CELL-ADHESION TO COMPONENTS OF EXTRACELLULAR-MATRIX PRODUCED BY STREPTOMYCES SP MJ654-NF4 .1. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL-ACTIVITIES [J].
AMEMIYA, M ;
UENO, M ;
OSONO, M ;
MASUDA, T ;
KINOSHITA, N ;
NISHIDA, C ;
HAMADA, M ;
ISHIZUKA, M ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1994, 47 (05) :536-540
[2]   Synthesis and biological evaluation of cytostatin analogues [J].
Bialy, L ;
Waldmann, H .
CHEMICAL COMMUNICATIONS, 2003, (15) :1872-1873
[3]  
Bialy L, 2002, ANGEW CHEM INT EDIT, V41, P1748, DOI 10.1002/1521-3773(20020517)41:10<1748::AID-ANIE1748>3.0.CO
[4]  
2-X
[5]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[6]  
DESS DB, 1983, J ORG CHEM, V48, P4156
[7]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE [J].
IRELAND, RE ;
LIU, LB .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2899-2899
[8]   Enantioselective total synthesis of taurospongin A [J].
Lebel, H ;
Jacobsen, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9624-9625
[9]   Synthesis of enantioenriched propargylic alcohols related to polyketide natural products. A comparison of methodologies [J].
Marshall, JA ;
Bourbeau, MP .
ORGANIC LETTERS, 2003, 5 (18) :3197-3199
[10]   Addition of allenylzinc reagents, prepared in situ from nonracemic propargylic mesylates, to aldehydes. A new synthesis of highly enantioenriched homopropargylic alcohols [J].
Marshall, JA ;
Adams, ND .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5201-5204