Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions
- 3 March 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (12) , 4098-4100
Abstract
Recent developments in the use of isonitriles to furnish secondary and tertiary amide bond formations have been applied to a novel total synthesis of the important cyclic polypeptide cyclosporine A. Specifically, the disclosed synthetic route demonstrates the utility of microwave-mediated carboxylic acid isonitrile couplings, thioacid isonitrile couplings at ambient temperature, and isonitrile-mediated couplings of carboxylic acids and thioacids with amines to form challenging amide bonds.Keywords
This publication has 32 references indexed in Scilit:
- A simple method for the conversion of carboxylic acids into thioacids with Lawesson’s reagentTetrahedron Letters, 2009
- Thio FCMA Intermediates as Strong Acyl Donors: A General Solution to the Formation of Complex Amide BondsJournal of the American Chemical Society, 2009
- Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitrilesTetrahedron Letters, 2009
- Thio-mediated two-component coupling reaction of carboxylic acids and isonitriles under mild conditionsTetrahedron Letters, 2009
- On the preparation of enantiomerically pure isonitriles from amino acid esters and peptidesTetrahedron Letters, 2009
- Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkagesNature Protocols, 2008
- Addressing Mechanistic Issues in the Coupling of Isonitriles and Carboxylic Acids: Potential Routes to Peptidic ConstructsJournal of the American Chemical Society, 2008
- On the Two-Component Microwave-Mediated Reaction of Isonitriles with Carboxylic Acids: Regarding Alleged Formimidate Carboxylate Mixed AnhydridesJournal of the American Chemical Society, 2008
- New Chemistry with Old Functional Groups: On the Reaction of Isonitriles with Carboxylic Acids—A Route to Various Amide TypesJournal of the American Chemical Society, 2008
- CyclosporinDrugs, 1993