Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P.

K Okumura, Y Nakamura, C Shin

Index: Okumura, Kazuo; Nakamura, Yutaka; Shin, Chung-Gi Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 7 p. 1561 - 1569

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Citation Number: 23

Abstract

The first total synthesis of a macrocyclic antibiotic, micrococcin P (1), was accomplished. After constructing the central 2, 3, 6-tristhiazolyl-substituted pyridine skeleton [Fragment A— C segment](21) from ethyl 2-(2-bromoacetyl-6-dimethoxymethyl-3-pyridyl) thiazole-4- carboxylate (15) in 11 steps, successive fragment condensations of 21 with ethyl 2-[(Z)-1-(Ot- butyldiphenylsilyl-L-threonylamino)-1-propenyl] thiazole-4-carboxylate (29) and (S)-1-(O- ...