title: A short formal synthesis of squalamine from a microbial metabolite.
abstract: A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1). Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.
authors.affiliation: Magainin Pharmaceuticals Inc., 5110 Campus Drive, Plymouth Meeting, Pennsylvania 19462, USA. wkinney1@prius.jnj.com
authors.forename: W A
authors.initials: WA
authors.lastname: Kinney
authors.forename: X
authors.initials: X
authors.lastname: Zhang
authors.forename: J I
authors.initials: JI
authors.lastname: Williams
authors.forename: S
authors.initials: S
authors.lastname: Johnston
authors.forename: R S
authors.initials: RS
authors.lastname: Michalak
authors.forename: M
authors.initials: M
authors.lastname: Deshpande
authors.forename: L
authors.initials: L
authors.lastname: Dostal
authors.forename: J P
authors.initials: JP
authors.lastname: Rosazza
mesh_terms: D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis*; D002777:Cholestanols / Q000138:chemical synthesis*; D006900:Hydroxylation; D003904:Mitosporic Fungi / Q000378:metabolism; D009654:Norsteroids / Q000737:chemistry / Q000378:metabolism
chemical_list: C414922:3-keto-23,24-bisnorchol-4-en-22-ol; D020533:Angiogenesis Inhibitors; D002777:Cholestanols; D009654:Norsteroids; C079655:squalamine