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Synfacts 2016; 12(09): 0885
DOI: 10.1055/s-0035-1562770
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (−)-Communesin F

Contributor(s):
Erick M. Carreira
,
Johannes Boshkow
Lathrop SP, Pompeo M, Chang W.-TT, Movassaghi M * Massachusetts Institute of Technology, Cambridge, USA
Convergent and Biomimetic Enantioselective Total Synthesis of (–)-Communesin F.

J. Am. Chem. Soc. 2016;
138: 7763-7769
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Publication History

Publication Date:
18 August 2016 (online)

 
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Key words

(−)-communesin F - alkaloids - late-stage heterodimerization - biomimetic synthesis

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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