Total synthesis of (-)-hennoxazole A |
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Authors: | Smith Thomas E Kuo Wen-Hsin Bock Victoria D Roizen Jennifer L Balskus Emily P Theberge Ashleigh B |
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Affiliation: | Department of Chemistry, Williams College, Williamstown, MA 01267, USA. tsmith@williams.edu |
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Abstract: | An enantioselective, convergent, total synthesis of the antiviral marine natural product (-)-hennoxazole A has been completed in 17 steps, longest linear sequence, from serine methyl ester and in 9 steps from an achiral bisoxazole intermediate. Elaboration of a thiazolidinethione allowed for rapid assembly of the pyran-based ring system. Key late-stage coupling was effected by deprotonation of the bisoxazole methyl group, followed by alkylation with an allylic bromide side chain segment. [structure: see text] |
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