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Organocatalyzed epoxidation in the total synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures†
Ajay Sharma,Satyendra Kumar Pandey
Organic & Biomolecular Chemistry Pub Date : 01/13/2023 00:00:00 , DOI:10.1039/D2OB02195A
Abstract

A simple, flexible and efficient organocatalyzed synthetic approach for the synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures has been described. The pivotal reaction sequence comprises organocatalyzed asymmetric Jørgensen epoxidation, Wittig olefination, migration of epoxide and Mitsunobu inversion reaction. Excellent enantiomeric purity (≥99%) was achieved during the synthesis of disparlure enantiomers by the Jørgensen epoxidation key step.

Graphical abstract: Organocatalyzed epoxidation in the total synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures
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