Indole Diterpene Synthetic Studies. Total Synthesis of (+)-Nodulisporic Acid F and Construction of the Heptacyclic Cores of (+)-Nodulisporic Acids A and B and (-)-Nodulisporic Acid D

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• 作者：Amos B. Smith ; III ; Akin H. Davulcu ; Young Shin Cho ; Kazuyuki Ohmoto ; Lá ; szló ; Kü ; rti ; Haruaki Ishiyama
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：June 22, 2007
• 年：2007
• 卷：72
• 期：13
• 页码：4596 - 4610
• 全文大小：464K
• 年卷期：v.72,no.13(June 22, 2007)
• ISSN：1520-6904

文摘

A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. Thestrategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocoldeveloped in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerableacid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparationof the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acidF, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)-nodulisporic acid D were achieved.