Tremorgenic Indole Alkaloids. The Total Synthesis of (−)-Penitrem D
Journal of the American Chemical Society2003Vol. 125(27), pp. 8228–8237
Citations Over TimeTop 11% of 2003 papers
Amos B. Smith, Naoki Kanoh, Haruaki Ishiyama, Noriaki Minakawa, Jon D. Rainier, Richard A. Hartz, Young Shin Cho, Haifeng Cui, William H. Moser
Abstract
A convergent, stereocontrolled total synthesis of the architecturally complex tremorgenic indole alkaloid (-)-penitrem D (4) has been achieved. Highlights of the synthesis include an efficient, asymmetric synthesis of the western hemisphere; the stereocontrolled assembly of the I-ring; discovery of a novel autoxidation to introduce the C(22) tertiary hydroxyl group, required for tremorgenic activity; union of fully elaborated eastern and western hemispheres, exploiting an indole synthetic protocol developed expressly for this purpose; and a late-stage, stereoselective construction of the A and F rings exploiting a Sc(OTf)(3-)promoted reaction cascade. The longest linear sequence leading to (-)-penitrem D (4) was 43 steps.
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