Synthetic studies of erythromycins. IV. Total synthesis of erythronolide A.

…, M Arai, K Tomooka, N Ohsawa, M Kinoshita

Index: Nakata; Arai; Tomooka; Ohsawa; Kinoshita Bulletin of the Chemical Society of Japan, 1989 ,  vol. 62,  # 8  p. 2618 - 2635

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Citation Number: 49

Abstract

The enantiospecific total synthesis of erythronolide A (1) through (9S)-9-deoxo-9- hydroxyerythronolide A (2) from the chiral C1–C6, C7–C9, and C10–C13 synthetic segments is described. The C10–C13 segment,(3R, 4R, 5R)-5-O-benzyl-2-iodo-3, 4-O- isopropylidene-4-methyl-1-heptene-3, 4, 5-triol (11) was synthesized in 16 steps and an 8.3% overall yield from D-ribose. The C7–C9 segment,(S)-(+)-2-(2-bromo-1-methylethyl)-1 ...