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Synfacts 2016; 12(09): 0885
DOI: 10.1055/s-0035-1562770
DOI: 10.1055/s-0035-1562770
Synthesis of Natural Products and Potential Drugs
Total Synthesis of (−)-Communesin F
Further Information
Publication History
Publication Date:
18 August 2016 (online)
Significance
The communesin alkaloids feature a fused heptacylic ring system containing two adjacent quaternary carbons. Movassaghi and co-workers describe an enantioselective synthesis of (−)-communesin F, a member of this intriguingly complex natural product family. Highlights include the biomimetic heterodimerization of A and B, and aminal exchange from H to J.
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Comment
Building blocks A and B were unified through displacement at the sulfamate, followed by oxidation to diazene F. The diazene was irradiated to give G as a single diastereomer under extrusion of nitrogen. After deprotection of the Boc groups, the aminal exchange was induced by t-BuOLi. The natural product was then obtained after deprotection.
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