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Issue 20, 2005
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Studies towards the synthesis of epothilone A via organoboranes

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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 C7–C21 fragment of epothilone A involving asymmetric alkoxyallyl- and crotylboration using α-pinene-derived reagents has also been described.

Graphical abstract: Studies towards the synthesis of epothilone A via organoboranes

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Publication details

The article was received on 09 Jun 2005, accepted on 24 Aug 2005 and first published on 15 Sep 2005


Article type: Paper
DOI: 10.1039/B508001K
Citation: Org. Biomol. Chem., 2005,3, 3812-3824
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    Studies towards the synthesis of epothilone A via organoboranes

    P. V. Ramachandran, J. S. Chandra, B. Prabhudas, D. Pratihar and M.Venkat R. Reddy, Org. Biomol. Chem., 2005, 3, 3812
    DOI: 10.1039/B508001K

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