Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs

M. Venkat Ram Reddy, Herbert C. Brown, P. Veeraraghavan Ramachandran

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42 Scopus citations

Abstract

Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the corresponding 6-substituted dihydropyran-2-ones. These were diastereoselectively epoxidized and regioselectively reduced to furnish optically pure analogs of statin drugs. This procedure allows for the development of a combinatorial library of analogs of these drugs.

Original languageEnglish (US)
Pages (from-to)239-243
Number of pages5
JournalJournal of Organometallic Chemistry
Volume624
Issue number1-2
DOIs
StatePublished - Apr 1 2001

Bibliographical note

Funding Information:
Financial assistance from the Purdue Borane Research Fund is gratefully acknowledged.

Keywords

  • Allylboration
  • Asymmetric synthesis
  • Epoxidation
  • Metathesis
  • Reduction

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