Improved synthesis of epothilone B employing alkylation of an alkyne for assembly of subunits |
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Authors: | White J D Sundermann K F Carter R G |
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Institution: | Department of Chemistry, Oregon State University, Corvallis 97331-4003, USA. james.white@orst.edu |
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Abstract: | formula: see text] A strategy for assembling the two principal modules of epothilone B was developed that merges an allylic bromide with a terminal acetylene to fabricate the C10-C11 bond of the macrocycle. The resulting alkyne was semihydrogenated to give a seco ester previously employed in our total synthesis of epothilone B. This new approach affords a more efficient route to the naturally occurring macrolide and to its 9,10-dehydro analogue. |
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