title: Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B.
abstract: An isomer-divergent synthesis of naturally occurring pericosines A and B is described starting from a known D-ribose derived ene-diol in 35% and 41% overall yields respectively of which the latter is the best synthetic method reported for pericosine B. The key features of this synthesis include the stereoselective NHK vinylation of the terminal aldehyde to the versatile diolefinic chiral intermediate and elegant conversions of the same to the corresponding final products via RCM (Ring Closing Metathesis).
authors.affiliation: Department of Chemistry, National Dong Hwa University, Hualien, 97401, Taiwan, ROC.
authors.forename: Subhankar
authors.initials: S
authors.lastname: Tripathi
authors.forename: Ajam Chand
authors.initials: AC
authors.lastname: Shaikh
authors.forename: Chinpiao
authors.initials: C
authors.lastname: Chen
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D008968:Molecular Conformation; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; C496389:pericosine B; D012765:Shikimic Acid