Total Synthesis of 8-Deshydroxyajudazol B

被引：24

作者：

Birkett, Stephen ^{[1
]}

Ganame, Danny ^{[1
]}

Hawkins, Bill C. ^{[1
]}

Meiries, Sebastien ^{[1
]}

Quach, Tim ^{[1
]}

Rizzacasa, Mark A. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Inst Bio21, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 08期

基金：

澳大利亚研究理事会;

关键词：

AJUDAZOL-A; CHONDROMYCES-CROCATUS; TRANSESTERIFICATION; HYDROBORATION; MYXOBACTERIA; CONVENIENT; ENANTIOMER; EFFICIENT; CATALYST; SYSTEM;

D O I：

10.1021/ol200331u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.

引用

页码：1964 / 1967

页数：4

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