Control of olefin geometry in the bryostatin B-ring through exploitation of a C2-symmetry breaking tactic and a Smith-Tietze coupling reaction

被引：43

作者：

Hale, KJ ^{[1
]}

Hummersone, MG ^{[1
]}

Bhatia, GS ^{[1
]}

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 15期

关键词：

D O I：

10.1021/ol005850y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A completely stereocontrolled asymmetric synthesis of an advanced a-ring synthon for the bryostatin family of antitumor agents is reported. Noteworthy features of our synthesis include the Smith-Tietze bis-alkylation reaction between 12 and 13 en route to C(2)-symmetrical ketone 10 and the totally stereoselective conversion of 10 into triol 18 via a Grignard addition tactic. Triol 18 was converted to epoxide 3 in nine steps, and an acid-catalyzed intramolecular Williamson etherification reaction completed the synthesis of 2.

引用

页码：2189 / 2192

页数：4

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