Organocatalyzed epoxidation in the total synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures. Issue 7 (24th January 2023)

• Record Type: Journal Article
• Authors: Sharma, Ajay; Pandey, Satyendra Kumar
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 7(2023)
• Page Start: 1514
• Page End: 1517
• Publication Date: 2023-01-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob02195a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A simple, flexible and efficient organocatalyzed synthetic approach for the total synthesis of (−)- trans -, (+)- trans - and (+)- cis -disparlures has been described. 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.