A Practical and Efficient Total Synthesis of Potent Insulinotropic (2S, 3R, 4S)??4??Hydroxyisoleucine through a Chiral N??Protected γ??Keto?螃窿?aminoester

S De Lamo Marin, C Catala, SR Kumar…

Index: De Lamo Marin, Sandra; Catala, Cedric; Kumar, Sreekantha Ratna; Valleix, Alain; Wagner, Alain; Mioskowski, Charles European Journal of Organic Chemistry, 2010 , # 21 p. 3985 - 3989

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Citation Number: 3

Abstract

Abstract (2S, 3R, 4S)-4-Hydroxyisoleucine, which exhibits remarkable insulinotropic activity, is expected to be a potent drug to treat type II diabetes. We propose herein a four-step synthesis of the enantiopure natural product on the basis of successive Mannich condensation, catalytic epimerization, N-para-methoxyphenyl deprotection, and diastereoselective reduction. This compact economical and scalable sequence enables to ...