An Efficient Synthesis of γ-Methylene-γ-butyrolactone (α'-Angelicalactone). Application to the Synthesis of Deoxyobtusilactone and Deoxyisoobtusilactone

Richard A. Amos, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review

Abstract

The mercury(II)-catalyzed cyclization of 4-pentynoic acid proceeds efficiently to give γ-methylene-γ-butyrolac-tone (α'-angelicalactone). The enolate of this lactone reacts with 11-dodecenal producing separable diastereomeric β-hydroxylactones. The corresponding methanesulfonate derivatives undergo partially selective elimination to afford deoxyobtusilactone and deoxyisoobtusilactone.

Original languageEnglish (US)
Pages (from-to)560-564
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number4
DOIs
StatePublished - 1978

ASJC Scopus subject areas

  • Organic Chemistry

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