Studies directed toward the total synthesis of azaspiracid.: Construction of the C1-C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system

被引：31
|
作者：
Carter, RG [1 ]
Graves, DE [1 ]
机构：
[1] Univ Mississippi, Dept Chem & Biochem, University, MS 38677 USA
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 35期
关键词：
D O I：
10.1016/S0040-4039(01)01211-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The efficient entry to the C-1-C-19 carbon backbone of azaspiracid is outlined utilizing a key Julia coupling strategy. Spirocyclization of a C-12 sulfone substrate induced formation of the unprecedented. nonnatural transoidal bisspiroketal. Construction of the bisspirocyclic array at C-10 and C-13, in the absence of the C-12 sulfone, led to formation of the cisoidal orientation of the bisspirocycle, with the nonnatural stereochemistry at C-13. (C) 2001 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码：6035 / 6039
页数：5
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