A Formal Synthesis of (-)-Mycalamide A

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• 作者：Barry M. Trost ; Hanbiao Yang ; and Gary D. Probst
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：January 14, 2004
• 年：2004
• 卷：126
• 期：1
• 页码：48 - 49
• 全文大小：61K
• 年卷期：v.126,no.1(January 14, 2004)
• ISSN：1520-5126

文摘

Novel strategies are developed for an efficient formal synthesis of (-)-mycalamide A. The left-hand side (-)-7-benzoylpederic acid is synthesized from (2S,3S)-2,3-epoxybutane. The key features include a highly regioselective Ru-catalyzed alkene-alkyne coupling reaction and a novel way to control the challenging C(7) stereocenter. The right-hand side was synthesized from (R)-pantolactone. The complex trioxodecalin core is constructed with two Pd(0)-catalyzed O--allyl cyclizations. The first one is chemoselective, while the second one is highly diastereoselective. Three additional steps would be required to complete a total synthesis of (-)-mycalamide A.