Stereoselective synthesis of (–)-tetrahydropyrenophorol

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Published: Sep 18, 2020
DOI: https://doi.org/10.2298/JSC190823040R
Keywords:
macrodiolide sharpless asymmetric dihydroxylation Mitsunobu reaction stereoselectivity

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Vyasabhattar Ramanujan
Division of Chemistry, Department of Sciences and Humanities, Vignan's Foundation for Science, Technology & Research (VFSTR) University, Vadlamudi, Guntur 522 213, Andhra Pradesh
Shaik Sadikha
Division of Chemistry, Department of Sciences and Humanities, Vignan's Foundation for Science, Technology & Research (VFSTR) University, Vadlamudi, Guntur 522 213, Andhra Pradesh
Chebolu Naga Sesha Sai Pavan Kumar
Division of Chemistry, Department of Sciences and Humanities, Vignan's Foundation for Science, Technology & Research (VFSTR) University, Vadlamudi, Guntur 522 213, Andhra Pradesh
https://orcid.org/0000-0003-4724-4937

Abstract

Tetrahydropyrenophorol, an interesting macrodiolide, was isolated from the plant Fagonia cretica. The total synthesis of (–)-1-tetrahydro­pyr­enophorol was achieved in an elegant and linear manner from readily an acces­sible racemic epoxide. The archetypal reactions include regioselective opening of the epoxide, Sharpless asymmetric dihydroxylation, and Mitsunobu cyclo­dimerization to construct the requisite 16-membered bis-lactone. The synthetic approach demonstrated here is very simple and could be used for the syntheses of related compounds in an economic and highly stereoselective way.

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How to Cite
[1]
V. Ramanujan, S. Sadikha, and C. N. S. S. P. Kumar, “Stereoselective synthesis of (–)-tetrahydropyrenophorol”, J. Serb. Chem. Soc., vol. 85, no. 9, pp. 1129–1136, Sep. 2020.
Issue
Vol. 85 No. 9 (2020)
Section
Organic Chemistry

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