Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

Tony K.M. Shing, Ching Hung Wong, Ting Yip

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.

Original languageEnglish
Pages (from-to)1323-1340
Number of pages18
JournalTetrahedron Asymmetry
Volume7
Issue number5
DOIs
Publication statusPublished - 1996 May

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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