A convergent synthesis of 14-membered FOG ring analogs of the teicoplanin binding pocket via intramolecular SNAr reaction

…, R Beugelmans, S Bourdet, J Chastanet…

Index: Zhu, Jieping; Beugelmans, Rene; Bourdet, Sebastien; Chastanet, Jacqueline; Roussi, George Journal of Organic Chemistry, 1995 , vol. 60, # 20 p. 6389 - 6396

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Citation Number: 47

Abstract

An intramolecular SNA~ reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-0-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization ...