Synfacts 2017; 13(10): 1007
DOI: 10.1055/s-0036-1591232
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Virosaine A

Contributor(s): Erick M. Carreira, Nicole Hauser
Hughes JM. E. Gleason JL. * McGill University, Montreal, Canada
A Concise Enantioselective Total Synthesis of (–)-Virosaine A.

Angew Chem. Int. Ed. 2017;
56: 10830-10834
Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Significance

Virosaine A is a highly congested, polycyclic member of the Securinega alkaloid family. In their elegant synthetic approach towards (–)-virosaine A, Gleason and Hughes rely on an epoxide opening to trigger the intramolecular [3+2] cycloaddition proposed in its biosynthesis.


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Comment

Epoxide opening in oxabicycle F afforded nitrone G, which underwent an intramolecular cycloaddition reaction to give the pentacyclic core structure H. Subsequent alcohol protection and regioselective lithiation/bromination afforded intermediate I, which was converted to (–)-virosaine A by a sequence of five more transformations.


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