Studies towards the synthesis of epothilone A via organoboranes

P. Veeraraghavan Ramachandran, J. Subash Chandra, Bodhuri Prabhudas, Debarshi Pratihar, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-γ,γ-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-dimethylhomoallylic alcohols in high enantioselectivities. The application of this reagent for the synthesis of the C1-C6 subunit of epothilone has been demonstrated. Alternatively, inter- and intramolecular asymmetric reduction protocols have also been utilized for the synthesis of the C1-C6 subunit of epothilone A. The synthesis of the C1-C2 fragment of epothilone A involving asymmetric alkoxyallyl- and crotylboration using α-pinene-derived reagents has also been described.

Original languageEnglish (US)
Pages (from-to)3812-3824
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume3
Issue number20
DOIs
StatePublished - Oct 21 2005

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