Dihydropyran as a template for lactone synthesis

Matthew P. Brichacek, Robert M Carlson

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


3,4-Dihydro-2H-pyran (DHP) was efficiently transformed into 4-thiophenyl-3,4-dihydro-2H-pyran. This intermediate was converted to the corresponding 1,3-O,S-allylic carbanion with t-butyllithium and selectively alkylated at the carbon α to the sulfur with alkyl halides, an epoxide, and an aldehyde. An one-pot oxidative elimination of the sulfur fragment using vanadium pentoxide generates the desired β-substituted α,β- unsaturated δ-valero lactone.

Original languageEnglish (US)
Pages (from-to)3541-3549
Number of pages9
JournalSynthetic Communications
Issue number20
StatePublished - Jan 2007

Bibliographical note

Copyright 2009 Elsevier B.V., All rights reserved.


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