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Vol. 29 No. 10 (2017): Vol 29 Issue 10

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

https://doi.org/10.14233/ajchem.2017.20816
Krishnaji Tadiparthi
Department of Chemistry, Christ University, Hosur Road, Bangalore-560 029, India; Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
S. Raghavendra
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India; Department of Pharmaceutical Chemistry, School of Pharmacy and Health Sciences, International Medical University, Kuala Lumpur 57000, Malaysia
Ahmed Kamal
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India

Corresponding Author(s) : Krishnaji Tadiparthi

krishnaji.tadiparthi@christuniversity.in; tkrishnaji@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 10 (2017): Vol 29 Issue 10

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
Tadiparthi, K., Raghavendra, S., & Kamal, A. (2017). Lipase-Catalyzed Resolution of 1-[4-(Benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-Centrolobine. Asian Journal of Chemistry, 29(10), 2321–2326. https://doi.org/10.14233/ajchem.2017.20816
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