title: Studies on oxidopyrylium [5+2] cycloadditions: toward a general synthetic route to the C12-hydroxydaphnetoxins.
abstract: [Structure: see text] 12-hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
authors.forename: Paul A
authors.initials: PA
authors.lastname: Wender
authors.forename: F Christopher
authors.initials: FC
authors.lastname: Bi
authors.forename: Nicole
authors.initials: N
authors.lastname: Buschmann
authors.forename: Francis
authors.initials: F
authors.lastname: Gosselin
authors.forename: Cindy
authors.initials: C
authors.lastname: Kan
authors.forename: Jung-Min
authors.initials: JM
authors.lastname: Kee
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Ohmura
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D001952:Bridged-Ring Compounds; D004224:Diterpenes