Diastereoselective [2,3] Wittig rearrangement of carbohydrate-derived tertiary allylic ethers. 1. Synthesis of the C11-C18 subunit of herbimycin a from D-glucose.

Jill E. Eshelman, Janet L. Epps, James Kallmerten

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21 Scopus citations

Abstract

Reductive fragmentation of the D-glucose derived iodopyranose 7 and diastereoselective [2,3] Wittig rearrangement of the resulting tertiary allylic ether affords trisubstituted olefin 19, comprising the C11-C18 segment of the benzoquinoid ansamycin herbimycin A.

Original languageEnglish (US)
Pages (from-to)749-752
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number5
DOIs
StatePublished - Jan 29 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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