title: Development of a concise synthesis of ouabagenin and hydroxylated corticosteroid analogues.
abstract: The natural product ouabagenin is a complex cardiotonic steroid with a highly oxygenated skeleton. This full account describes the development of a concise synthesis of ouabagenin, including the evolution of synthetic strategy to access hydroxylation at the C19 position of a steroid skeleton. In addition, approaches to install the requisite butenolide moiety at the C17 position are discussed. Lastly, methodology developed in this synthesis has been applied in the generation of novel analogues of corticosteroid drugs bearing a hydroxyl group at the C19 position.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Hans
authors.initials: H
authors.lastname: Renata
authors.forename: Qianghui
authors.initials: Q
authors.lastname: Zhou
authors.forename: Georg
authors.initials: G
authors.lastname: Dünstl
authors.forename: Jakob
authors.initials: J
authors.lastname: Felding
authors.forename: Rohan R
authors.initials: RR
authors.lastname: Merchant
authors.forename: Chien-Hung
authors.initials: CH
authors.lastname: Yeh
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D000305:Adrenal Cortex Hormones / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D008968:Molecular Conformation; D010042:Ouabain / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000305:Adrenal Cortex Hormones; D010042:Ouabain; C008721:ouabagenin