A divergent approach to apoptolidin and FD-891: asymmetric preparation of a common intermediate

被引:21
作者
Chng, SS [1 ]
Xu, J [1 ]
Loh, TP [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
apoptolidin; FD-891; divergent synthesis;
D O I
10.1016/S0040-4039(03)01173-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Biologically active Apoptolidin and FD-891 have structural similarity in their macrocyclic cores. Asymmetric preparation of a common intermediate in the total synthesis of these two macrolides is presented. A modified Masuyama Sn-allylation was employed to control the relative stereochemistry in the synthesis of the intermediate. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4997 / 5000
页数:4
相关论文
共 21 条
[1]   Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891 [J].
Eguchi, T ;
Kobayashi, K ;
Uekusa, H ;
Ohashi, Y ;
Mizoue, K ;
Matsushima, Y ;
Kakinuma, K .
ORGANIC LETTERS, 2002, 4 (20) :3383-3386
[2]   Structure of apoptolidin, a specific apoptosis inducer in transformed cells [J].
Hayakawa, Y ;
Kim, JW ;
Adachi, H ;
Shin-ya, K ;
Fujita, K ;
Seto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3524-3525
[3]   STEREOSELECTIVE SYNTHESES OF BUILDING-BLOCKS WITH 3 CONSECUTIVE STEREOGENIC CENTERS - IMPORTANT PRECURSORS OF POLYKETIDE NATURAL-PRODUCTS [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (06) :489-503
[4]   Regio- and diastereocontrol in carbonyl allylation by 1-halobut-2-enes with tin(II) halides [J].
Ito, A ;
Kishida, M ;
Kurusu, Y ;
Masuyama, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :494-498
[5]  
Kim JW, 1997, J ANTIBIOT, V50, P628
[6]   THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].
MARYANOFF, BE ;
REITZ, AB .
CHEMICAL REVIEWS, 1989, 89 (04) :863-927
[7]   FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S [J].
NAGAOKA, H ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (23) :3873-3888
[8]   Synthesis of the macrocyclic core of apoptolidin [J].
Nicolaou, KC ;
Li, YW ;
Weyershausen, B ;
Wei, HX .
CHEMICAL COMMUNICATIONS, 2000, (04) :307-308
[9]  
Nicolaou KC, 2001, ANGEW CHEM INT EDIT, V40, P3849, DOI 10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO
[10]  
2-M