title: Synthesis of clionamine B, an autophagy stimulating aminosteroid isolated from the sponge Cliona celata.
abstract: Clionamine B (2), an aminosteroid isolated from the marine sponge Cliona celata, has been synthesized starting from the plant sapogenin tigogenin (5). A key step in the synsthesis is the stereoselective introduction of the C-20 α-hydroxyl substituent via oxidation of a γ-lactone enolate with molecular oxygen. Synthetic clionamine B (2) strongly stimulated autophagy in human breast cancer MCF-7 cells.
authors.affiliation: Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, B. C., Canada, V6T 1Z1.
authors.forename: Roberto
authors.initials: R
authors.lastname: Forestieri
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Donohue
authors.forename: Aruna
authors.initials: A
authors.lastname: Balgi
authors.forename: Michel
authors.initials: M
authors.lastname: Roberge
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
mesh_terms: D000818:Animals; D001343:Autophagy / Q000187:drug effects*; D001943:Breast Neoplasms / Q000737:chemistry / Q000378:metabolism / Q000473:pathology*; D006801:Humans; D061986:MCF-7 Cells / Q000737:chemistry*; D008386:Marine Biology; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D013256:Steroids; C587230:clionamine B