Stereoselective route to oxetanocin carbocyclic analogues based on a [2 + 2] photocycloaddition to a chiral 2(5H)-furanone

Albert Rustullet, Ramon Alibés, Pedro De March, Marta Figueredo, Josep Font

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35 Citations (Scopus)

Abstract

The synthesis of the trisubstituted cyclobutane 7, which is a suitable precursor for the preparation of oxetanocin carbocyclic analogues, is described. The key step involves a regio- and diastereoselective [2 + 2] photochemical reaction of ketene diethyl acetal with (S)-5-pivaloyloxymethyl-2(5H)-furanone, 3. As an application of this methodology, (-)-cyclobut-A has been prepared from the intermediate 7. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)2827-2830
JournalOrganic Letters
Volume9
Issue number15
DOIs
Publication statusPublished - 19 Jul 2007

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