Studies towards the synthesis of epothilone A via organoboranes |
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Authors: | Ramachandran P Veeraraghavan Chandra J Subash Prabhudas Bodhuri Pratihar Debarshi Reddy M Venkat Ram |
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Affiliation: | Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, IN 47907-2084, USA. chandran@purdue.edu |
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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-gamma,gamma-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding alpha,alpha-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 alpha-pinene-derived reagents has also been described. |
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