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

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,...

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Bibliographic Details
Published in:Synlett 2009-01, Vol.2009 (2), p.233-236
Main Authors: McErlean, Christopher S., Willis, Anthony C.
Format: Article
Language:English
Subjects:
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0028-1087519