The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one

S. Chandrasekhar, Ch Narsihmulu, S. Shameem Sultana, M. Srinivasa Reddy

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia.

Original languageEnglish (US)
Pages (from-to)9299-9301
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number50
DOIs
StatePublished - Dec 6 2004
Externally publishedYes

Bibliographical note

Funding Information:
We C.N., S.S.S., and M.S.R. thank CSIR New Delhi for financial support and S.C. thanks DST, New Delhi for a grant.

Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.

Keywords

  • Keck asymmetric allylation
  • Maruoka asymmetric allylation
  • Ring-closing metathesis

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