Lipase-catalyzed resolution of 1-[4-(benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-centrolobine

Title

Lipase-catalyzed resolution of 1-[4-(benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-centrolobine

Creator

Tadiparthi K.; Raghavendra S.; Kamal A.

Description

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. 2017, Chemical Publishing Co. All rights reserved.

Source

Asian Journal of Chemistry, Vol-29, No. 10, pp. 2321-2326.

Date

2017-01-01

Publisher

Chemical Publishing Co.

Subject

Enantioselectivity; Kinetic resolution; Lipases; Metathesis; Mitsunobu reaction

Coverage

Tadiparthi K., Department of Chemistry, Christ University, Hosur Road, Bangalore, 560 029, India, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500 007, India; Raghavendra S., 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; Kamal A., Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500 007, India

Rights

All Open Access; Bronze Open Access

Relation

ISSN: 9707077; CODEN: AJCHE

Format

Online

Language

English

Type

Article

Identifier

https://doi.org/10.14233/ajchem.2017.20816

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