A Practical Synthesis of (2S, 3R, 4S)??4??Hydroxyisoleucine, A Potent Insulinotropic α??Amino Acid from Fenugreek

…, J Ouazzani, NA Sasaki, P Potier

Index: Wang, Qian; Ouazzani, Jamal; Andre Sasaki; Potier, Pierre European Journal of Organic Chemistry, 2002 , # 5 p. 834 - 839

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Citation Number: 26

Abstract

Abstract An efficient eight-step synthesis of optically pure (2S, 3R, 4S)-4-hydroxyisoleucine (1), a potent insulinotropic α-amino acid found in the seeds of fenugreek (Trigonella foenum- graecum L.), is achieved in 39% overall yield. The method is suitable for large-scale production of the title compound. The key steps involve the biotransformation of ethyl 2- methylacetoacetate to ethyl (2S, 3S)-2-methyl-3-hydroxybutanoate (2) with Geotrichum ...