Tremorgenic indole alkaloids. Studies directed toward the assembly of the A, F, and I rings of penitrem D: Observation of an unexpected stereochemical outcome

Amos B. Smith, Naoki Kanoh, Noriaki Minakawa, Jon D. Rainier, Frances R. Blase, Richard A. Hartz

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

(matrix presented) In this Letter we demonstrate the viability of a highly stereoselective tandem Mannich cyclization-grammine fragmentation/addition cascade, critical for assembly of the A and F rings of penitrem D. We also explored simultaneous execution of this tactic with concurrent construction of ring I. Reinvestigation of a model system provided an explanation for the unanticipated stereochemical outcome at C(28).

Original languageEnglish
Pages (from-to)1263-1266
Number of pages4
JournalOrganic letters
Volume1
Issue number8
DOIs
Publication statusPublished - 1999 Oct 21

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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