title: Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone.
abstract: Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate. Key features of the syntheses include the stereoselective construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones via a Pd(0)-catalyzed intramolecular allylic alkylation, and the facile transformation of the common intermediate into natural iridoids.
authors.affiliation: College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea. ygsuh@snu.ac.kr.
authors.forename: Jaehoon
authors.initials: J
authors.lastname: Sim
authors.forename: Inah
authors.initials: I
authors.lastname: Yoon
authors.forename: Hwayoung
authors.initials: H
authors.lastname: Yun
authors.forename: Hongchan
authors.initials: H
authors.lastname: An
authors.forename: Young-Ger
authors.initials: YG
authors.lastname: Suh
mesh_terms: D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D039823:Iridoids / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes; D039823:Iridoids; D007783:Lactones; D011753:Pyrones; C115644:nepetalactone