Grace J. Drummond , Phillip S. Grant , Alisha M. Geurts , Daniel P. Furkert , Margaret A. Brimble
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引用次数: 0
摘要
帕拉莫内酯 A 是一种 7,8-seco-labdane萜类化合物，具有独特的双环[2.2.2]辛烷核心和一个螺丁烯内酯分子。本研究报告通过 10 个步骤对双环丁烯内酯核心进行了生物模拟合成，其特点包括意想不到的自氧化开环和乙烯基 Mukaiyama 醛醇反应，该反应之后自发地发生了不寻常的分子内乙烯基醛醇反应，从而组装了帕拉莫内酯 A 的螺丁烯内酯分子和双环核心。
Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach†
Pallamolide A is a 7,8-seco-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.
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