Pyrylium salts in polyene natural product synthesis: Organometallic additions to 4-methylpyrylium tetrafluoroborate

Richard J.K. Taylor, Karl Hemming, Edna Faria De Medeiros

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised. The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described. Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.

Original languageEnglish
Pages (from-to)2385-2392
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number19
DOIs
Publication statusPublished - 1 Dec 1995
Externally publishedYes

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