Six-Step Synthesis of Alcyopterosin A, a Bioactive Illudalane Sesquiterpene with a gem-Dimethylcyclopentane Ring

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• 作者：Tung T. Hoang ; Mélodie Birepinte ; Nicholas J. Kramer ; Gregory B. Dudley
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：18
• 期：14
• 页码：3470-3473
• 全文大小：323K
• 年卷期：0
• ISSN：1523-7052

文摘

Strategic pairing of ring openings and cycloisomerization provides rapid and efficient “open and shut” entry into sparsely functionalized illudalanes, as exemplified here in the context of a six-step synthesis of alcyopterosin A. Key steps include a tandem ring-opening fragmentation/olefination process for preparing a neopentyl-tethered 1,6-enyne, ring-opening olefination telescoped with alkyne homologation, and Rh-catalyzed oxidative cycloisomerization.