Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids

Gary E. Keck; Erik N.K. Cressman; Eric J. Enholm

doi:10.1021/jo00279a022

Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids

Gary E. Keck, Erik N.K. Cressman, Eric J. Enholm

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

52 Scopus citations

Abstract

Syntheses of (±)-isoretronecanol, (±)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed. The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction of the azabicyclo[3.3.0] ring system. The stereochemistry of the cyclization process, which affords almost exclusively the less stable C₂-endo products, is discussed.

Original language	English (US)
Pages (from-to)	4345-4349
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	54
Issue number	18
DOIs	https://doi.org/10.1021/jo00279a022
State	Published - Sep 1 1989
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00279a022

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abstract = "Syntheses of (±)-isoretronecanol, (±)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed. The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction of the azabicyclo[3.3.0] ring system. The stereochemistry of the cyclization process, which affords almost exclusively the less stable C2-endo products, is discussed.",

author = "Keck, {Gary E.} and Cressman, {Erik N.K.} and Enholm, {Eric J.}",

year = "1989",

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T1 - Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis

T2 - Applications to Pyrrolizidine Alkaloids

AU - Keck, Gary E.

AU - Cressman, Erik N.K.

AU - Enholm, Eric J.

PY - 1989/9/1

Y1 - 1989/9/1

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AB - Syntheses of (±)-isoretronecanol, (±)-supinidine, (-)-dihydroxyheliotridane, and (+)-heliotridine are detailed. The key step in each case involves an intramolecular acyliminium ion cyclization onto a suitably positioned allylstannane for construction of the azabicyclo[3.3.0] ring system. The stereochemistry of the cyclization process, which affords almost exclusively the less stable C2-endo products, is discussed.

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Intramolecular Allylstannane Cyclizations in Alkaloid Synthesis: Applications to Pyrrolizidine Alkaloids

Abstract

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