Total Synthesis of (-)-Reveromycin A via a Hetero-Diels-Alder Approach

被引：6

作者：

El Sous, Mariana ^{[1
]}

Ganame, Danny ^{[1
]}

Tregloan, Peter ^{[1
]}

Rizzacasa, Mark A. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

SYNTHESIS-STUTTGART | 2010年 / 23期

基金：

澳大利亚研究理事会;

关键词：

reveromycin; 6,6]-spiroketal; hetero-Diels-Alder; high-pressure acylation; Stille coupling; EPIDERMAL-GROWTH-FACTOR; EUKARYOTIC CELL-GROWTH; REVEROMYCIN-A; BIOLOGICAL-ACTIVITIES; SPIROKETALS; INHIBITORS; ACID; STEREOCHEMISTRY; DERIVATIVES; ALDEHYDES;

D O I：

10.1055/s-0030-1258308

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of (-)-reveromycin A is described which utilizes a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the labile [6,6]-spiroketal core in a highly stereo-selective manner. An asymmetric syn-aldol reaction installed the stereochemistry at C4-C5 whilst a Stille cross coupling was utilized to form the C21-C22 bond. The C18 hemisuccinate was formed by high pressure acylation reaction and a final Wittig extension followed by global deprotection with tetrabutylammonium fluoride gave (-)-reveromycin A.

引用

页码：3954 / 3966

页数：13

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