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Synthesis 2015; 47(05): 653-658
DOI: 10.1055/s-0034-1379709
DOI: 10.1055/s-0034-1379709
paper
Stereoselective Total Synthesis of Pinolide and Its C2 Epimer and Evaluation of Their Cytotoxic Activity[1]
Further Information
Publication History
Received: 19 September 2014
Accepted after revision: 19 November 2014
Publication Date:
11 December 2014 (online)
Abstract
Pinolide, a naturally occurring nonenolide and its C2 epimer have been synthesized using d-mannitol and 1,2-epoxyhex-5-ene as the starting materials. The synthesis involves the Jacobsen’s hydrolytic kinetic resolution, Yamaguchi esterification, and intramolecular ring-closing metathesis as the key steps. The 2-epi-pinolide, the C2 epimer of pinolide, has been synthesized for the first time. The cytotoxic activity of the pinolide and 2-epi-pinolide has been studied.
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References and notes
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