Stereoselective synthesis of (-)-tetrahydropyrenophorol

Journal of the Serbian Chemical Society

Sadikha Shaik¹  Pavan Kumar Chebolu Naga Sesha Sai¹  Ramanujan Vyasabhattar¹ 

[1] Division of Chemistry, Department of Sciences and Humanities, Vignan’s Foundation for Science, Technology & Research (VFSTR) University, Vadlamudi, Guntur, Andhra Pradesh, India;

关键词: macrodiolide;    sharpless asymmetric dihydroxylation;    mitsunobu reaction;    stereoselectivity;   

DOI  :  10.2298/JSC190823040R

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown