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Synthesis 2024; 56(19): 3027-3036
DOI: 10.1055/a-2338-4149
DOI: 10.1055/a-2338-4149
paper
Diastereodivergent Synthesis of A-Ring Lactones Derived from Cholesterol and Diosgenin: A Convenient Solution for an Old Problem – NMR and X-ray Characterization
W.H.G.S. thanks Consejo Nacional de Ciencia y Tecnología (CONAHCyT) for the fellowship granted (CVU 695425). Financial support was provided by Dirección General de Asuntos del Personal Académico, Universidad Nacional Autónoma de México (Grant IN204323) and the Faculty of Chemistry, Universidad Nacional Autónoma de México (PAIP-5000-9063).
Abstract
A convenient protocol for the synthesis of A-ring lactones derived from cholesterol was developed. A lactone reduction–lactol separation–reoxidation sequence, applied to the inseparable mixture of diastereomeric lactones, allows the production of multigram amounts of each lactone in pure form. The same sequence applied to A-ring lactones derived from diosgenin produced similar results. A detailed NMR characterization of all the obtained lactones is also provided. X-ray diffraction corroborated the structure of the obtained compounds.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2338-4149.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. April 2024
Angenommen nach Revision: 04. Juni 2024
Accepted Manuscript online:
04. Juni 2024
Artikel online veröffentlicht:
20. Juni 2024
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