title: Scalable and divergent total synthesis of (+)-colletoic acid, a selective 11β-hydroxysteroid dehydrogenase type 1 inhibitor.
abstract: An efficient and divergent total synthesis of (+)-colletoic acid, a selective 11-β hydroxysteroid dehydrogenase 1 (11-βHSD1) inhibitor, is presented along with its biological activity at the whole-cell level. A scalable, asymmetric synthetic strategy was designed featuring a diversity-oriented synthesis utilizing a diastereoselective intramolecular 5-exo-Heck reaction as the key step to provide the quaternary spirocenter intermediate 9 in multigram scale, thus establishing a platform for further structure-activity relationship studies and providing access to other acorane family members.
authors.affiliation: Department of Chemical Biology and Therapeutics, St. Jude Children's Research Hospital , Memphis, Tennessee 38105-3678, United States.
authors.forename: Taotao
authors.initials: T
authors.lastname: Ling
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Griffith
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Mitachi
authors.forename: Fatima
authors.initials: F
authors.lastname: Rivas
mesh_terms: D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1 / Q000037:antagonists & inhibitors* / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D012717:Sesquiterpenes; C532324:colletoic acid; D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1