Formal synthesis of amphidinin B

被引：14
|
作者：
Krishna, Palakodety Radha [1 ]
Anitha, Kadimi [1 ]
Raju, Galla [1 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India
来源：
TETRAHEDRON | 2013年 / 69卷 / 05期
关键词：
Cytotoxicity; Evans aldol; Julia olefination; Oxa-Michael; Keck allylation; Evans asymmetric alkylation; Yamaguchi esterification; STEREOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; T1; T4;
D O I：
10.1016/j.tet.2012.11.075
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, convergent, and highly stereoselective formal synthesis of amphidinin B (1) is reported herein. In Amphidinin B both C10-C21 (4) and C1-C9 (5) fragments were derived from geraniol 6 and mono-PMB ether of 1,4-butane diol 7 in 19 and 9 steps, respectively. The key steps involved in this synthesis are Sharpless asymmetric epoxidation, Evans aldol, Julia olefination, oxa-Michael, Keck allylation, Mannich reaction, Evans asymmetric alkylation, and Yamaguchi esterification. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1649 / 1657
页数：9
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