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

doi:10.1021/ol9909379

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 journal › Article › peer-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 language	English
Pages (from-to)	1263-1266
Number of pages	4
Journal	Organic letters
Volume	1
Issue number	8
DOIs	https://doi.org/10.1021/ol9909379
Publication status	Published - 1999 Oct 21
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9909379

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Tremorgenic indole alkaloids. Studies directed toward the assembly of the A, F, and I rings of penitrem D : Observation of an unexpected stereochemical outcome. / Smith, Amos B.; Kanoh, Naoki; Minakawa, Noriaki; Rainier, Jon D.; Blase, Frances R.; Hartz, Richard A.

In: Organic letters, Vol. 1, No. 8, 21.10.1999, p. 1263-1266.

Research output: Contribution to journal › Article › peer-review

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AU - Hartz, Richard A.

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

Abstract

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