An improved one-pot method for the stereoselective synthesis of the (2S, 3R)-3-amino-2-hydroxy acids: key intermediates for bestatin and amastatin

R Herranz, J Castro-Pichel, S Vinuesa…

Index: Herranz; Castro-Pichel; Vinuesa; Garcia-Lopez Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2232 - 2234

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Citation Number: 79

Abstract

several reaction conditions (Table I) gave a mixture of the threo and erythro 0-(trimethylsily1) cyanohydrins 4 and 5, which could not be separated. This mixture was directly transformed into the corresponding 2-hydroxy esters 6 and 7 by treatment with dry methanolic hydrogen chloride (3: l EbO/MeOH, saturated with HCl, 0" C, 24 h), followed by in situ hydrolysis (< lo" C, 24-48 h) 15 of the imidate hydrochloride intermediate. The methyl esters 6 and 7 were ...