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Studies towards the synthesis of epothilone A via organoboranes†
P. Veeraraghavan Ramachandran,J. Subash Chandra,Bodhuri Prabhudas,Debarshi Pratihar,M.Venkat Ram Reddy
Organic & Biomolecular Chemistry Pub Date : 09/15/2005 00:00:00 , DOI:10.1039/B508001K
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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