Photochemical cycloaddition of mono-, 1,1-, and 1,2-disubstituted olefins to a chiral 2(5H)-furanone. Diastereoselective synthesis of (+)-lineatin

Marta Racamonde, Ramon Alibés, Marta Figueredo, Josep Font, Pedro De March

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22 Citations (Scopus)

Abstract

(Chemical Equation Presented) The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6. © 2008 American Chemical Society.
Original languageEnglish
Pages (from-to)5944-5952
JournalJournal of Organic Chemistry
Volume73
Issue number15
DOIs
Publication statusPublished - 1 Aug 2008

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