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Paper | Special issue | Vol 101, No. 2, 2020, pp.645-663
Published online, 3rd October, 2019
DOI: 10.3987/COM-19-S(F)55
α-L-Vancosamine Aryl C-Glycosides, Less Stable Anomers: A Problem in Synthesis of Pluramycin-Class Antibiotics

Yoshio Ando, Hiromune Asahina, Kei Kitamura, Takashi Matsumoto, and Keisuke Suzuki*

*Chemistry, Tokyo Institute of Technology, 2-12-1,Oh-Okayama, Meguro-ku, Tokyo 152-8552, Japan

Abstract

The pluramycin-class antibiotics have attracted considerable synthetic interest by their bioactivities and unique chemical structures. By the thermodynamic disadvantage, the selective formation of the aryl α-C-glycoside of an L-vancosamine motif, commonly embedded in this class of natural products, has been one of the problems in their total synthesis. This paper summarizes the stereochemical behavior of the pluramycin-class natural products and reports the results of our model study to address this issue by examining three L-vancosaminyl donors under Lewis acidic conditions.