A facile synthesis of N-protected statine and analogs via a lipase-catalyzed kinetic resolution

• Published in: Journal of organic chemistry Vol. 58; no. 15; pp. 4010 - 4012
• Main Authors: Baenziger, Markus, McGarrity, John F, Meul, Thomas
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.1993; Amer Chemical Soc
• Subjects: Aliphatic compounds; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Chemistry; Chemistry, Organic; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; ORGANIC-SYNTHESIS; ASYMMETRIC-SYNTHESIS; (3S,4S)-STATINE; AMINO; EFFICIENT SYNTHESIS; STEREOSPECIFIC SYNTHESIS; TETRAMIC-ACID; STEREOSELECTIVE SYNTHESIS; RENIN INHIBITORS; (3S,4S)-CYCLOHEXYLSTATINE; Fungi; Candida cylindracea; α-Aminoacid; Hydroxyacid; Enzyme; Aliphatic compound; Optical resolution; Trans stereoisomer; Triacylglycerol lipase; Fungi Imperfecti; Thallophyta; Enzymatic reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00067a038

A new synthesis of N-protected statine 4a and its analogue 4b is presented. cis-(+/-)-Butyric acid 2-isobutyl-5-oxopyrrolidin-3-yl ester (10a) and cis-(+/-)-butyric acid 2-benzyl-5-oxopyrrolidin-3-yl ester (10b) were prepared from methyl (E)-4-chloro-3-methoxybut-2-enoate (5) and subsequently resolved via a kinetic resolution catalyzed by Candida Cylindracea lipase. The desired enantiomers were isolated in excellent enantiomeric excess and good yield. These products were then converted to the N-BOC-protected hydroxy amino acids 4a and 4b.