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

Authors
Smith, AB Kanoh, N Minakawa, N Rainier, JD Blase, FR Hartz, RA
Citation
Ab. Smith et al., Tremorgenic indole alkaloids, studies directed toward the assembly of the A, F, and I rings of penitrem D: Observation of an unexpected stereochemical outcome, ORG LETT, 1(8), 1999, pp. 1263-1266
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
8
Year of publication
1999
Pages
1263 - 1266
Database
ISI
SICI code
1523-7060(19991021)1:8<1263:TIASDT>2.0.ZU;2-2
Abstract
[GRAPHICS] In this Letter we demonstrate the viability of a highly stereoselective tan dem Mannich cyclization-grammine fragmentation/addition cascade, critical f or assembly of the A and F rings of penitrem D. We also explored simultaneo us execution of this tactic with concurrent construction of ring I. Reinves tigation of a model system provided an explanation for the unanticipated st ereochemical outcome at C(28).