title: Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide.
abstract: The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).
authors: Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors: Takashi
authors: T
authors: Sawada
authors: Masahisa
authors: M
authors: Nakada
mesh_terms: D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1 / Q000037:antagonists & inhibitors*; D043303:Aryldialkylphosphatase / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001391:Azo Compounds; D002264:Carboxylic Acids; D003521:Cyclopropanes; D012717:Sesquiterpenes; C532324:colletoic acid; C030797:cyclopropane; D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1; D043303:Aryldialkylphosphatase