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  • Title: Total synthesis of (-)-hennoxazole A.
    Author: Smith TE, Kuo WH, Bock VD, Roizen JL, Balskus EP, Theberge AB.
    Journal: Org Lett; 2007 Mar 15; 9(6):1153-5. PubMed ID: 17316014.
    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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