Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine

DL Boger, K Takahashi

文献索引：Boger, Dale L.; Takahashi, Kanji Journal of the American Chemical Society, 1995 , vol. 117, # 50 p. 12452 - 12459

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被引用次数: 34

摘要

Abstract: Concise total syntheses of the naturally occurring tropoloisoquinolines grandirubrine (l), imerubrine (2), and isoimerubrine (3) are detailed. The regioselective total synthesis of grandirubrine (1) is based on the [4+ 21 cycloaddition reaction of the a-pyrone 44 with the cyclopropenone ketal 18. Subsequent retro-Diels-Alder loss of C02, norcaradiene rearrangement to the cycloheptatrienone ketal, and ketal hydrolysis ...