Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine

Krishnaji Tadiparthi1,2,*, S. Raghavendra2,3 and Ahmed Kamal2

1Department of Chemistry, Christ University, Hosur Road, Bangalore-560 029, India

2Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India

3Department of Pharmaceutical Chemistry, School of Pharmacy and Health Sciences, International Medical University, Kuala Lumpur 57000, Malaysia

*Corresponding author: E-mail: krishnaji.tadiparthi@christuniversity.in; tkrishnaji@gmail.com

Abstract

A practical and efficient method for the preparation of homoallylic alcohol and its successful enzymatic resolution has been developed. This lipase-catalyzed resolution process has been optimized with respect to different lipases and solvents. Moreover, Mitsunobu strategy has been applied to recover the unwanted isomer. Further optically enriched homoallylic alcohol has been employed for the synthesis of (-)-centrolobine.

Keywords

Kinetic resolution, Lipases, Enantioselectivity, Mitsunobu reaction and Metathesis.

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