Preparative-scale synthesis of both antipodes of B-γ,γ- dimethylallyldiisopinocampheylborane: Application for the synthesis of C 1-C6 subunit of epothilone

P. Veeraraghavan Ramachandran, Bodhuri Prabhudas, J. Subash Chandra, M. Venkat Ram Reddy, Herbert C. Brown

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Abstract

A preparative-scale synthesis of B-γ,γ- dimethylallyldiisopinocampheylborane starting from prenyl alcohol has been described. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-dimethylhomoallylic alcohols in high enantioselectivities. The application of this reagent has been demonstrated for the synthesis of C1-C6 subunit of epothilone.

Original languageEnglish (US)
Pages (from-to)1011-1013
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number5
DOIs
StatePublished - Jan 26 2004

Keywords

  • B-Methoxydiisopinocampheylborane
  • Dimethylallylboration
  • Epothilone
  • Prenyl alcohol

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