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Application of an Intramolecular Stetter Reaction to Access trans,syn,trans -Fused Pyrans

Date

2009

Authors

McErlean, Christopher S P
Willis, Anthony

Journal Title

Journal ISSN

Volume Title

Publisher

Georg Thieme Verlag

Abstract

The use of a commercially available thiazolium salt facilitated an intramolecular Stetter reaction between an aliphatic aldehyde and an acrylate unit, which delivered a trans,syn-fused bicyclic pyranone in high yield as a single diastereomer. The pyranone was used to synthesize a trans,syn,trans-fused polycyclic ether array and was ring expanded to give the corresponding oxepanone.

Description

Keywords

Keywords: Carbenes; Diastereoselectivity; Fused-ring systems; Ring closure; Umpolung

Citation

Source

Synlett

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1055/s-0028-1087519

Restricted until

2037-12-31