A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

Jothi L. Nallasivam; Rodney A. Fernandes

doi:10.1039/C6OB02398C

A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

Jothi L. Nallasivam^a and Rodney A. Fernandes*^a

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^a Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India
E-mail: rfernand@chem.iitb.ac.in
Fax: +91 22 25767152
Tel: +91 22 25767174

Abstract

A collective synthesis of a γ-butyrolactone class of paraconic acids such as (+)-methylenolactocin, (+)-phaseolinic acid, (+)-nephrosteranic acid, (+)-nephrosterinic acid, (+)-rocellaric acid and (+)-protolichesterinic acid is described. The strategy adopted is protecting-group-free based on efficient Pd-catalyzed Suzuki–Miyaura coupling and Ru-catalyzed Sharpless oxidation to construct the core β-CO₂H-γ-butyrolactone unit to accomplish the synthesis of various paraconic acids.

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Publication details

The article was received on 03 Nov 2016, accepted on 12 Dec 2016 and first published on 12 Dec 2016

Article type: Paper

DOI: 10.1039/C6OB02398C

Citation: Org. Biomol. Chem., 2017,15, 708-716

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A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

J. L. Nallasivam and R. A. Fernandes, Org. Biomol. Chem., 2017, 15, 708
DOI: 10.1039/C6OB02398C
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Organic & Biomolecular Chemistry

A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

Abstract

Supplementary files

Publication details

A protecting-group-free synthesis of (+)-nephrosteranic, (+)-protolichesterinic, (+)-nephrosterinic, (+)-phaseolinic, (+)-rocellaric acids and (+)-methylenolactocin

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