Tremorgenic Indole Alkaloids. The Total Synthesis of (-)-Penitrem D

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• 作者：Amos B. Smith ; III* ; Naoki Kanoh ; Haruaki Ishiyama ; Noriaki Minakawa ; Jon D. Rainier ; Richard A. Hartz ; Young Shin Cho ; Haifeng Cui ; and William H. Moser
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：July 9, 2003
• 年：2003
• 卷：125
• 期：27
• 页码：8228 - 8237
• 全文大小：407K
• 年卷期：v.125,no.27(July 9, 2003)
• ISSN：1520-5126

文摘

A convergent, stereocontrolled total synthesis of the architecturally complex tremorgenic indolealkaloid (-)-penitrem D (4) has been achieved. Highlights of the synthesis include an efficient, asymmetricsynthesis of the western hemisphere; the stereocontrolled assembly of the I-ring; discovery of a novelautoxidation to introduce the C(22) tertiary hydroxyl group, required for tremorgenic activity; union of fullyelaborated eastern and western hemispheres, exploiting an indole synthetic protocol developed expresslyfor this purpose; and a late-stage, stereoselective construction of the A and F rings exploiting aSc(OTf)_3-promoted reaction cascade. The longest linear sequence leading to (-)-penitrem D (4) was 43steps.