Enantioselective Total Syntheses of Cassane Furanoditerpenoids and Their Stimulation of Cellular Respiration in Brown Adipocytes

We report the first and enantioselective total syntheses of (+)-1-deacetylcaesalmin C, (+)-δ-caesalpin, (+)-norcaesalpinin MC, and (+)-norcaesalpinin P. Salient features of the synthetic strategy are an exo-selective intramolecular Diels–Alder reaction of a furanoquinone monoketal and subsequent che...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-10, Vol.145 (39), p.21562-21568
Main Authors: Bulthaupt, Hendrik H., Glatz, Fabian, Papidocha, Sven M., Wu, Chunyan, Teh, Shawn, Wolfrum, Susanne, Balážová, Lucia, Wolfrum, Christian, Carreira, Erick M.
Format: Article
Language:English
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Summary:We report the first and enantioselective total syntheses of (+)-1-deacetylcaesalmin C, (+)-δ-caesalpin, (+)-norcaesalpinin MC, and (+)-norcaesalpinin P. Salient features of the synthetic strategy are an exo-selective intramolecular Diels–Alder reaction of a furanoquinone monoketal and subsequent chemoselective reduction of the resulting pentacyclic furfuryl ketal, furnishing a keystone intermediate. The latter enables access to the collection of natural products through implementation of stereoselective oxidations. Having accessed the cassane furanoditerpenoids, we unveil previously unknown bioactivity: (+)-1-deacetylcaesalmin C stimulates respiration in brown adipocytes, which has been suggested to play a central role in treatment of obesity.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c07597