Synthesis 2013; 45(14): 1991-1996
DOI: 10.1055/s-0033-1338799
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Pinellic Acid

Sunil Kumar Sunnam
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India   Fax: +91(80)23600529   Email: prasad@orgchem.iisc.ernet.in
,
Kavirayani R. Prasad*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India   Fax: +91(80)23600529   Email: prasad@orgchem.iisc.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 08 March 2013

Accepted after revision: 18 April 2013

Publication Date:
17 May 2013 (online)


Abstract

A straightforward strategy for the synthesis of (+)-pinellic acid in 16% overall yield and 13 steps, starting from (1R)-1-(furan-2-yl)hexan-1-ol, is described. Key reactions in the synthesis include a Sharpless kinetic resolution, oxidation of a protected furan to reveal a but-2-ene-1,4-dione moiety, and an asymmetric reduction.

Supporting Information