Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D

Amos B. Smith, Naoki Kanoh, Haruaki Ishiyama, Noriaki Minakawa, Jon D. Rainier, Richard A. Hartz, Young Shin Cho, Haifeng Cui, William H. Moser

Research output: Contribution to journalArticle

67 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8228-8237
Number of pages10
JournalJournal of the American Chemical Society
Volume125
Issue number27
DOIs
Publication statusPublished - 2003 Jul 9

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Smith, A. B., Kanoh, N., Ishiyama, H., Minakawa, N., Rainier, J. D., Hartz, R. A., Cho, Y. S., Cui, H., & Moser, W. H. (2003). Tremorgenic indole alkaloids. The total synthesis of (-)-penitrem D. Journal of the American Chemical Society, 125(27), 8228-8237. https://doi.org/10.1021/ja034842k