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Org. Biomol. Chem., 2005, 3, 3812 - 3824, DOI: 10.1039/b508001k

Studies towards the synthesis of epothilone A via organoboranes

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

Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-,-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding ,-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 -pinene-derived reagents has also been described.

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