Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Naoyuki Hanaki, J. T. Link, David W.C. MacMillan, Larry E. Overman, William G. Trankle, Julie A. Wurster

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

(matrix presented) The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the α-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.

Original languageEnglish (US)
Pages (from-to)223-226
Number of pages4
JournalOrganic Letters
Volume2
Issue number2
DOIs
StatePublished - Jan 27 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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