Total Synthesis of Calicheamicin γ1I.1. Synthesis of the Oligosaccharide Fragment

R. D. Groneberg, T. Miyazaki, N. A. Stylianides, T. J. Schulze, W. Stahl, E. P. Schreiner, T. Suzuki, Y. Iwabuchi, A. L. Smith, K. C. Nicolaou

Research output: Contribution to journalArticlepeer-review

133 Citations (Scopus)

Abstract

The first total synthesis of the calicheamicin γ1I oligosaccharide fragment in the form of its methyl glycoside (62) has been achieved. The synthetic challenge of the B-ring was recognized and studied initially, resulting in a novel and unique solution to the stereochemical problems posed involving a [3, 3]-sigmatropic rearrangement of an allylic thionoimidazolide (111). This chemistry was initially worked out on a model for the ABC-ring system (47) and then successfully applied to the real system. The success of this synthesis has enabled the completion of the first synthesis of the natural product itself, calicheamicin γ1I (1), as will be described in the following papers in this issue.

Original languageEnglish
Pages (from-to)7593-7611
Number of pages19
JournalJournal of the American Chemical Society
Volume115
Issue number17
DOIs
Publication statusPublished - 1993 Aug 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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