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Synthetic access to bent polycycles by cation-pi cyclization.

ABSTRACT: The presence of an ether oxygen within a chain undergoing cation-polyene cyclization has a profound influence on the stereochemistry of this important construction, apparently due to nucleophilic participation of oxygen in the cyclization process and formation of an oxonium intermediate, leading to bent fused ring systems.

SUBMITTER: Shenvi RA

PROVIDER: S-EPMC2914341 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Synthetic access to bent polycycles by cation-pi cyclization.

Shenvi Ryan A RA Corey E J EJ

Organic letters 20100801 15

The presence of an ether oxygen within a chain undergoing cation-polyene cyclization has a profound influence on the stereochemistry of this important construction, apparently due to nucleophilic participation of oxygen in the cyclization process and formation of an oxonium intermediate, leading to bent fused ring systems. ...[more]

PMID: 20670018

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