Phosphate-tether-mediated ring-closing metathesis for the preparation of complex 1,3-anti-diol-containing subunits

Rambabu Chegondi, Soma Maitra, Jana L. Markley, Paul R. Hanson

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

An array of examples of diastereoselective, phosphate-tether-mediated ring-closing metathesis reactions, which highlight the importance of product ring size and substrate stereochemical compatibility, as well as complexity, is reported. Studies focus primarily on the formation of bicyclo[n.3.1]phosphates, involving the coupling of C2-symmetric dienediol subunits with a variety of simple, as well as complex, alcohol partners. Phosphate-tether mediation: An array of examples of diastereoselective, phosphate-tether-mediated ring-closing metathesis reactions, which highlight the importance of product ring size and substrate stereochemical complexity, is reported (see scheme). Bicyclo[n.3.1]phosphates can be prepared utilizing the tripodal coupling of C2-symmetric dienediol subunits with a variety of simple, as well as complex alcohol partners.

Original languageEnglish (US)
Pages (from-to)8088-8093
Number of pages6
JournalChemistry - A European Journal
Volume19
Issue number25
DOIs
StatePublished - Jun 17 2013

Keywords

  • bicyclic phosphate
  • diastereotopic differentiation
  • natural products
  • phosphate tether
  • ring-closing metathesis

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