title: First comprehensive bakkane approach: stereoselective and efficient dichloroketene-based total syntheses of (+/-)- and (-)-9-acetoxyfukinanolide, (+/-)- and (+)-bakkenolide A, (-)-bakkenolides III, B, C, H, L, V, and X, (+/-)- and (-)-homogynolide A, (+/-)-homogynolide B, and (+/-)-palmosalide C.
abstract: Cycloaddition of dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro beta-methylene-gamma-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol isomers.
authors.affiliation: Chimie Recherche (LEDSS), Université Joseph Fourier, BP 53X, 38041 Grenoble, France.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Brocksom
authors.forename: Fernando
authors.initials: F
authors.lastname: Coelho
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Deprés
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Greene
authors.forename: Marco E
authors.initials: ME
authors.lastname: Freire De Lima
authors.forename: Olivier
authors.initials: O
authors.lastname: Hamelin
authors.forename: Benoît
authors.initials: B
authors.lastname: Hartmann
authors.forename: Alice M
authors.initials: AM
authors.lastname: Kanazawa
authors.forename: Yanyun
authors.initials: Y
authors.lastname: Wang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000737:chemistry; D053138:Cyclohexenes; D004000:Dichloroethylenes / Q000737:chemistry*; D036901:Petasites / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D003510:Cyclohexanes; D053138:Cyclohexenes; D004000:Dichloroethylenes; D012717:Sesquiterpenes; C052568:cyclohexene; C039586:dichloroketene; D015107:4-Butyrolactone; C016257:bakkenolide A