Total synthesis of (±)-photodeoxytridachione through a Lewis acid catalyzed cyclization

Aubry K. Miller; Dirk Trauner

doi:10.1002/anie.200390158

Total synthesis of (±)-photodeoxytridachione through a Lewis acid catalyzed cyclization

Aubry K. Miller, Dirk Trauner

Chemistry

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

Abstract

Concerted or stepwise: The concise total synthesis of the molluscan polypropionate photodeoxytridachione (3) features a Lewis acid catalyzed cyclization of tetraenoic ester 1 to form bicylo[3.1.0]hexene 2 as a key step. The stereochemistry of the cyclization can be rationalized in terms of a stepwise or a concerted mechanism.

Original language	English (US)
Pages (from-to)	549-552
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	42
Issue number	5
DOIs	https://doi.org/10.1002/anie.200390158
State	Published - Feb 3 2003

Keywords

Cyclization
Cycloaddition
Homogeneous catalysis
Lewis acids
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200390158

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abstract = "Concerted or stepwise: The concise total synthesis of the molluscan polypropionate photodeoxytridachione (3) features a Lewis acid catalyzed cyclization of tetraenoic ester 1 to form bicylo[3.1.0]hexene 2 as a key step. The stereochemistry of the cyclization can be rationalized in terms of a stepwise or a concerted mechanism.",

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KW - Lewis acids

KW - Total synthesis

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Total synthesis of (±)-photodeoxytridachione through a Lewis acid catalyzed cyclization

Abstract

Keywords

ASJC Scopus subject areas

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