Synthesis of the functionalized tricyclic core of lactonamycin by oxidative dearomatization

被引：62

作者：

Cox, C

Danishefsky, SJ

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

[2] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10024 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 22期

关键词：

D O I：

10.1021/ol006531+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report in this Letter a synthesis of the densely oxygenated CDEF ring system (27) corresponding to that found in the recently discovered antibiotic lactonamycin. The key steps in the synthesis consist of an intramolecular Wessely oxidative lactonization of acid 18, followed by a hydroxyl directed epoxidation of enol ether 21.

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页码：3493 / 3496

页数：4

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