title: Synthesis of the shark repellent pavoninin-4.
abstract: [reaction: see text] The first synthesis of the shark repellent pavoninin-4, 3, was achieved in 12 steps with 21% overall yield from diosgenin, 8. Key reactions involve an efficient synthesis of the C-15alpha hydroxyl steroid from a C-16beta hydroxyl steroid by an unexpected 1,2-transposition strategy, a stereospecific glycosylation of a hindered C-15alpha alcohol using glycosyl fluoride as a glycosyl donor and a highly chemoselective acetylation of the C-26 primary alcohol by catalytic transesterification.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. john.r.williams@temple.edu
authors.forename: John R
authors.initials: JR
authors.lastname: Williams
authors.forename: Hua
authors.initials: H
authors.lastname: Gong
authors.forename: Nathan
authors.initials: N
authors.lastname: Hoff
authors.forename: Olaoluwa I
authors.initials: OI
authors.lastname: Olubodun
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012754:Sharks
chemical_list: D000617:Aminoglycosides; D002784:Cholesterol; C507447:pavoninin-4