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Total Syntheses of (+)-Stemarin and the Proposed Structures of Stemara-13(14)-en-18-ol and Stemara-13(14)-en-17-acetoxy-18-ol

Jialei Hu, Ziqi Jia, Kaixiang Xu, Hanfeng Ding

2020Organic Letters17 citationsDOI

Abstract

An asymmetric and efficient approach for the total syntheses of (+)-stemarin and the proposed structures of stemara-13(14)-en-18-ol and stemara-13(14)-en-17-acetoxy-18-ol are described. The key features of the strategy include a Lewis acid-induced cationic polyene cyclization and an ODI-[5+2] cycloaddition/pinacol-type 1,2-acyl migration cascade.

Topics & Concepts

ChemistryPolyeneCationic polymerizationCycloadditionStereochemistryLewis acids and basesPinacolTotal synthesisCascadeOrganic chemistryCatalysisChromatographyBioactive Natural Diterpenoids ResearchPlant-based Medicinal ResearchAdvanced Synthetic Organic Chemistry
Total Syntheses of (+)-Stemarin and the Proposed Structures of Stemara-13(14)-en-18-ol and Stemara-13(14)-en-17-acetoxy-18-ol | Litcius