Convergent access to polycyclic cyclopentanoids from a,b-unsaturated acid chlorides and alkynes through a reductive coupling, Nazarov cyclization sequence

Jason Hugh Chaplin, Kristal Emily Jackson, Jonathan White, Bernard Luke Flynn

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Abstract

Reductive coupling of a,?-unsaturated acid chlorides A with alkynoyls B provides convergent access to Nazarov cyclization precursors, a-carboxy divinyl ketones C. Cyclization of C gives an intermediate oxyallyl cation intermediate D, which can be trapped with tethered arenes (Ar). The resultant products can be further cyclized through nucleophilic displacement of suitable leaving groups X by tethered OH groups to give lactones (in a subsequent step). Where X is a suitable chiral auxiliary (e.g., oxazolidinone) this strategy affords access to homochiral cyclopentanoids
Original languageEnglish
Pages (from-to)3659 - 3664
Number of pages6
JournalThe Journal of Organic Chemistry
Volume79
Issue number8
DOIs
Publication statusPublished - 2014

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