Total Synthesis of an Antitumor Agent RA-VII via an Efficient Preparation of Cycloisodityrosine

A Bigot, ME Tran Huu Dau, J Zhu

Index: Bigot, Antony; Tran Huu Dau, Marie Elise; Zhu, Jieping Journal of Organic Chemistry, 1999 ,  vol. 64,  # 17  p. 6283 - 6296

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Citation Number: 44

Abstract

Details of efficient syntheses of (9 S, 12 S)-cycloisodityrosine (6) and a concise total synthesis of RA-VII (1) were described. An intramolecular SNAr-based cycloetherification reaction was employed as the key ring-closure step for construction of the illusive 14- membered m, p-cyclophane. Treatment of methyl N-[N-(tert-butyloxycarbonyl)-l-(3-hydroxy-4- methoxyphenylalanyl]-l-4-fluoro-3-nitrophenylalaninate ((9 S, 12 S)-10) with potassium ...