An enantiospecific synthesis of the C-21-C-37 segment of the aglycon of amphotericin B.

M Kinoshita, H Takami, M Taniguchi…

Index: Kinoshita; Takami; Taniguchi; Tamai Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 6 p. 2151 - 2161

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Citation Number: 26

Abstract

3-Deoxy-1, 2-O-isopropylidene-3-C-methyl-α-D-allofuranose was stereoselectively converted into 3, 5-dideoxy-4-O-(methoxymethyl)-3, 5-di-C-methyl-6-O-pivaloyl-L-talose ethylene dithioacetal (31) via 3, 5-dideoxy-4-O-(methoxymethyl)-3, 5-di-C-methyl-L- talopyranuro-6, 2-lactone ethylene dithioacetal (24) in 10 steps (23.6% overall yield). Desulfurization [Raney Ni W-4, 92% yield] of 31 followed by three-step transformation (91 ...