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

Full Text: HTML

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 ...

Related Articles:

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

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

Synthesis of 4-Hydroxyisoleucine by the Aldolase–Transaminase Coupling Reaction and Basic Characterization of the Aldolase from Arthrobacter simplex AKU 626

[Bioscience, Biotechnology and Biochemistry, , vol. 71, # 7 p. 1607 - 1615]

Synthesis of hydantoin analogues of (2S, 3R, 4S)-4-hydroxyisoleucine with insulinotropic properties

[Bioorganic and Medicinal Chemistry Letters, , vol. 18, # 15 p. 4332 - 4335]

More Articles...