The Journal of organic chemistry

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

BW Gung, G Kumi

文献索引：Gung, Benjamin W.; Kumi, Godwin Journal of Organic Chemistry, 2004 , vol. 69, # 10 p. 3488 - 3492

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被引用次数: 37

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-Chodkiewicz coupling reaction affording the entriyne unit. The bromoalkyne 6 with an ω-carboxylic acid group was found to undergo a copper-catalyzed cross-coupling reaction producing the desired diyne intermediate 10, ...