Total synthesis of (S)-(-)-(E)-15,16-dihydrominquartynoic acid:: A highly potent anticancer agent

被引：41

作者：

Gung, BW ^{[1
]}

Kumi, G ^{[1
]}

机构：

[1] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 10期

关键词：

D O I：

10.1021/jo049920g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugated entriyne natural product, (S)-(E)-15,16-dihydrominquartynoic acid (1), is synthesized in five linear steps and 30% overall yield from the known aldehyde 11. The key step is a one-pot in situ desilylation/Cadiot-Chodkiewiez coupling reaction affording the entriyne unit. The bromoalkyne 6 with an omega-carboxylic acid group was found to undergo a copper-catalyzed cross-coupling reaction producing the desired diyne intermediate 10, while the corresponding omega-ester bromoalkyne 14 failed to couple with triethylsilylacetylene under a variety of conditions.

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页码：3488 / 3492

页数：5

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