Total synthesis of (-)-hennoxazole A.


Journal Article

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]

Full Text

Duke Authors

Cited Authors

  • Smith, TE; Kuo, W-H; Bock, VD; Roizen, JL; Balskus, EP; Theberge, AB

Published Date

  • March 2007

Published In

Volume / Issue

  • 9 / 6

Start / End Page

  • 1153 - 1155

PubMed ID

  • 17316014

Pubmed Central ID

  • 17316014

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol070244p


  • eng