A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A

被引：37

作者：

Crimmins, MT ^{[1
]}

McDougall, PJ ^{[1
]}

Emmitte, KA ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 18期

关键词：

D O I：

10.1021/ol051543m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. ant Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent assembly strategy was employed that relied on a Horner-Wadsworth-Emmons union of two complex fragments. Subsequent cyclization and dehydration led to efficient generation of an intermediate endocyclic enol ether, which was advanced to a tetracyclic fragment.

引用

页码：4033 / 4036

页数：4

共 57 条

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