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Synfacts 2005(0): 0002-0002  
DOI: 10.1055/s-2005-865340
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York

A Synthesis of Virantmycin via Enzyme-Mediated Diester Desymmetrization

Contributor(s): Philip Kocienski
T. G. Back*, J. E. Wulff
University of Calgary, Canada
A Stereodivergent Synthesis of Virantmycin by an Enzyme-Mediated Diester Desymmetrization and a Highly Hindered Aryl Amination
Angew. Chem. Int. Ed.  2004,  43:  6493-6496  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

palladium - amination - Curtius rearrangement - esterase - desymmetrization

Significance

(-)-Virantmycin was isolated from Streptomyces nitrosporeus. It has antifungal activity and it inhibits RNA and DNA viruses.

Comment

Key steps to the target molecule were (a) the pig liver esterase-mediated desymmetrization of the malonate A (89%, ee = 95%); (b) use of a Curtius rearrangement (B to C) to create the α-quaternary formamide; (c) a rare Pd-catalyzed intramolecular aryl amination (C to D) of an amine derivative with an α-quaternary center. The Keay ligand L was crucial to the success of the aryl amination.

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