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Published on: June 13, 2022
Practical and scalable enantioselective synthesis of (+)-majoranolide from Cyrene
Harald Podversnik1, Jason E Camp2, Ben W Greatrex1
1Faculty of Medicine and Health, University of New England, Armidale, NSW, 2351, Australia. ben.greatrex@une.edu.au.
Abstract:
A two-step enantioselective gram scale synthesis of the Persea derived γ-lactones (+)-majoranolide and (+)-majoranolide B has been achieved. The sequence uses the amine promoted crossed condensation of the biorenewable synthon Cyrene with aliphatic aldehydes followed by a Baeyer-Villiger oxidation. Comparison of optical rotation data with the natural products established the absolute configuration of the natural product series, and this work represents the first synthesis of these alkylidene natural products.
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