Diastereoselective synthesis of the 19-epi-C18-C25 segment of (-)-lasonolide A and an unusual inversion at C19

被引:10
作者
Yoshimura, T [1 ]
Bando, T [1 ]
Shindo, M [1 ]
Shishido, K [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
基金
日本学术振兴会;
关键词
polyketide; lasonolide A; radical cyclization; inversion; tamao oxidation;
D O I
10.1016/j.tetlet.2004.10.071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diastereoselective construction of the 19-epi-C-18-C-25 segment of (-)-lasonolide A was achieved using a 5-exo-trigonal mode of radical cyclization for the creation of the contiguous quaternary and tertiary stereogenic centers at C-22 and C-23 as the key reaction step. During the dehydration stage, it was found that an unusual inversion of configuration took place. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9241 / 9244
页数:4
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