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Total Synthesis of (−)-Communesin F
Convergent and Biomimetic Enantioselective Total Synthesis of (–)-Communesin F.
J. Am. Chem. Soc. 2016;
18 August 2016 (online)
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.
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.