title: Redox refunctionalization of steroid spiroketals. Structure correction of ritterazine M.
abstract: The structure of the North spiroketal moiety of ritterazine M has been corrected from 1a to 1b. This was accomplished by comparison of published spectra of the natural product with five synthetic spiroketal-alcohols. Synthesis of these models was efficiently accomplished by reductive cleavage of the spiroketal and Sharpless asymmetric dihydroxylation of an isopentyl, methyl 1,1-disubstituted olefin, followed by Suarez iodine[III] oxidative spirocyclization of monoprotected 1 degree,3 degree 1,2 diols.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: Seongmin
authors.initials: S
authors.lastname: Lee
authors.forename: Thomas G
authors.initials: TG
authors.lastname: LaCour
authors.forename: Douglas
authors.initials: D
authors.lastname: Lantrip
authors.forename: Philip L
authors.initials: PL
authors.lastname: Fuchs
mesh_terms: D015394:Molecular Structure; D010084:Oxidation-Reduction; D010619:Phenazines; D013141:Spiro Compounds / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry*
chemical_list: D010619:Phenazines; D013141:Spiro Compounds; D013256:Steroids; C448328:ritterazine M