Studies toward the Synthesis of Palhinine Lycopodium Alkaloids: A Morita–Baylis–Hillman/Intramolecular Diels–Alder Approach

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• 作者：Nicholas Sizemore ; Scott D. Rychnovsky
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：16
• 期：3
• 页码：688-691
• 全文大小：286K
• ISSN：1523-7052

文摘

A synthetic route to the isotwistane core of palhinine lycopodium alkaloids is described. A Morita鈥揃aylis鈥揌illman/intramolecular Diels鈥揂lder (IMDA) strategy sets the vicinal all-carbon quaternary centers present in this family of natural products. The regioselectivity of the IMDA reaction is dictated by the conditions employed for silyl enol ether formation, with one set of conditions providing the core of cardionine and alternate conditions generating the desired isotwistane core of isopalhinine.