Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 125, Issue 27, Pages 8228-8237Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja034842k
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- NIGMS NIH HHS [GM 29028] Funding Source: Medline
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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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