A Nitrile Oxide Based Entry to 2,3-Dihydropyran-4-ones. Synthesis of a Protected Version of “Compactin Lactone” in Racemic and Optically Active Forms

Alan P. Kozikowski, Chun Sing Li

Research output: Contribution to journalArticlepeer-review

Abstract

The use of nitrile oxides bearing a masked β-oxo group as β-hydroxy-3-oxopropionylating agents for the vicinal functionalization of olefins is described. The β-hydroxy ketones revealed on hydrogenation of the initially formed 1,3-dipolar cycloaddition products undergo zinc triflate promoted cyclocondensation to 2,3-dihydropyran-4-ones, useful carbohydrate building blocks. The application of this chemistry to the preparation of a protected form of “compactin lactone” is detailed.

Original languageEnglish (US)
Pages (from-to)778-785
Number of pages8
JournalJournal of Organic Chemistry
Volume50
Issue number6
DOIs
StatePublished - Mar 1985

ASJC Scopus subject areas

  • Organic Chemistry

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