Total Synthesis of Aigialomycin D Using a Ramberg-Backlund/RCM Strategy

被引：56

作者：

Baird, Lynton J. ^{[1
]}

Timmer, Mattie S. M. ^{[1
]}

Teesdale-Spittle, Paul H. ^{[2
]}

Harvey, Joanne E. ^{[1
]}

机构：

[1] Victoria Univ Wellington, Sch Chem & Phys Sci, Wellington, New Zealand

[2] Victoria Univ Wellington, Sch Biol Sci, Ctr Biodiscovery, Wellington, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 06期

关键词：

ALPHA; BETA-UNSATURATED ESTERS; SELECTIVE REDUCTION; RING; ROUTE; STEREOCHEMISTRY; MECHANISM; SULFONES; ACID;

D O I：

10.1021/jo802561s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bioactive resorcylic acid lactone aigialomycin D (1) has been synthesized by a novel combination of ring-closing metathesis (RCM) and Ramberg-Backlund reactions. This synthetic strategy enables the C1'-C2' alkene to be masked as a sulfone during formation of the macrocycle by ring closing metathesis at the C7'-C8' olefin, thus avoiding competing formation of a cyclohexene. A subsequent Ramberg-Backlund reaction efficiently produces the C1'-C2' E-alkene. This combined RCM/Ramberg-Backlund reaction strategy should be widely applicable to the synthesis of macrocyclic dienes.

引用

页码：2271 / 2277

页数：7

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