The dolastatins. 19. synthesis of dolaisoleuine

…, JK Srirangam, F Hogan-Pierson…

Index: Pettit; Singh; Srirangam; Hogan-Pierson; Williams Journal of Organic Chemistry, 1994 , vol. 59, # 7 p. 1796 - 1800

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Citation Number: 23

Abstract

The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBut), a 0-methoxy-y-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl-(S, S)-isoleucinal and tert-butyl acetate followed by 0-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical ...

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