Application of Highly Stereocontrolled Glycosidations Employing 2,6-Anhydro-2-thio Sugars to the Syntheses of Erythromycin A and Olivomycin A Trisaccharide

Kazunobu Toshima, Yuko Nozaki, Satsuki Mukaiyama, Tetsuro Tamai, Masaya Nakata, Kuniaki Tatsuta, Mitsuhiro Kinoshita

研究成果: Article査読

51 被引用数 (Scopus)

抄録

The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly α-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-L-altropyranoside (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly β-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (23), which was realized by employing TMSOTf, and the highly α-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.

本文言語English
ページ(範囲)3717-3727
ページ数11
ジャーナルJournal of the American Chemical Society
117
13
DOI
出版ステータスPublished - 1995 4

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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