Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D |
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Authors: | Smith Amos B Kanoh Naoki Ishiyama Haruaki Minakawa Noriaki Rainier Jon D Hartz Richard A Cho Young Shin Cui Haifeng Moser William H |
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Affiliation: | Department of Chemistry, Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu |
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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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