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Synfacts 2005(0): 0002-0002
DOI: 10.1055/s-2005-865340
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 KocienskiT. 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
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
Further Information
Publication History
Publication Date:
20 July 2005 (online)
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.