title: Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.
abstract: The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product.
authors.affiliation: Tri-Institutional PhD Program in Chemical Biology, Laboratory for Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center , 1275 York Avenue, New York, New York 10065, United States.
authors.forename: Adam M
authors.initials: AM
authors.lastname: Levinson
mesh_terms: D001230:Aspergillus / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D001688:Biological Products; D002219:Carbamates; D026121:Indole Alkaloids; C000588428:aspeverin; D007455:Iodine