Practical and scalable enantioselective synthesis of (+)-majoranolide from Cyrene

Title
Practical and scalable enantioselective synthesis of (+)-majoranolide from Cyrene
Publication Date
2024-02-07
Author(s)
Podversnik, Harald
Camp, Jason E
Greatrex, Ben W
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Royal Society of Chemistry
Place of publication
United Kingdom
DOI
10.1039/D3OB01919E
UNE publication id
une:1959.11/59535
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.

Link
Citation
Organic & Biomolecular Chemistry, 22(5), p. 950-953
ISSN
1477-0539
1477-0520
Start page
950
End page
953

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