Highly Stereocontrolled Synthesis of 2,6-Dideoxy Sugars and its Application to Synthesis of Natural Products

Kazunobu Toshima, Kuniaki Tatsuta

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Novel methodologies for stereocontrolled synthesis of 2,6-dideoxy sugars by efficient use of 2,6-anhydro-2-thio sugar and its application to synthesis of natural products are described. This article involves highly stereocontrolled and powerful glycosylations of 2,6-anhydro-2-thio sugar for synthesis of 2,6-dideoxy-α- and β-glycosides and highly sterecontrolled creations of C-3 configuration of 2,6-dideoxy sugar by an addition of a nucleophilic reagent to 2,6-anhydro-2-thio sugar. Further, the efficient total synthesis of erythromycin A, which is a most typical and clinically important macrolide antibiotic, from (9S)-9-dihydroerythronolide A is achieved by the successful application of the present novel methodologies.

Original languageEnglish
Pages (from-to)303-315
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume50
Issue number4
DOIs
Publication statusPublished - 1992
Externally publishedYes

Keywords

  • (9 S)-9-Dihydroerythronolide A
  • 2,6-Anhydro-2-thio sugar
  • 2,6-Dideoxy sugar
  • Erythromycin A
  • Stereocontrolled glycosylation
  • Stereocontrolled nucleophilic addition

ASJC Scopus subject areas

  • Organic Chemistry

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