General Synthesis of 1-Oxaspiro[4.5]decan-2-ones and 1-Oxaspiro[4.5]decanes from 5-Methylene-2(5H)-furanone

Daniel Alonso, Josep Font, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

28 Citations (Scopus)

Abstract

5-Methylene-2(5H)-furanone underwent Diels-Alder cycloadditions to butadiene and several acyclic and cyclic C-substituted dienes, respectively, affording bicyclic and tricyclic spiroadducts in good yields. These compounds are precursors of other unsaturated and saturated spirolactones and also spiroethers, which were obtained through simple chemical reactions, i.e., hydrogenation of C-C double bonds, reduction of the carbonyl group, and Michael addition. The synthesis of 32 spirolactones and eight spiroethers illustrates the scope and efficiency of this method. Many of these products are suitable for use as components of perfumes and aromas owing to their olfactive properties. © 1991, American Chemical Society. All rights reserved.
Original languageEnglish
Pages (from-to)5567-5572
JournalJournal of Organic Chemistry
Volume56
Issue number19
DOIs
Publication statusPublished - 1 Sep 1991

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