Highly stereoselective total synthesis of tylonolide, the aglycon of the 16-membered macrolide antibiotic tylosin. II. Total synthesis of tylonolide by virtue of 4- …

…, Y OIKAWA, T HAMADA, O YONEMITSU

Index: Tanaka; Oikawa; Hamada; Yonemitsu Chemical and Pharmaceutical Bulletin, 1987 , vol. 35, # 6 p. 2219 - 2227

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Citation Number: 13

Abstract

Tylonolide, was synthesized from D-glucose via coupling and cyclization of two segments i (2)(C-11-C-17) and ii (3)(C-1-C-10), which were synthesized from diacetoneglucose. A Prelog-Djerassi lactone-type compound was an intermediate in the synthesis of the latter segment. Esterification of the two segments by Yamaguchi's method followed by macrocyclization by use of the Wittig-Horner reaction gave the 16-membered cyclic enone ...