title: Confirmation of the configuration of 10-isothiocyanato-4-cadinene diastereomers through synthesis.
abstract: The marine sponge metabolite 10-isothiocyanato-4-cadinene (1) was first isolated by Garson et al. from Acanthella cavernosa in 2000. The same structure 1 was later reported by Wright et al. from the nudibranch Phyllidiella pustulosa and its sponge diet, but with different NMR data. The syntheses of both enantiomers of 1 were accomplished through the isothiocyanation of 10-isocyano-4-cadinene (2) previously synthesized by our group. The correct spectroscopic data and specific rotation value of the structure 1 were determined on the basis of the syntheses. The NMR data of synthetic 1 matched those of the isothiocyanate isolated by Garson and differed from those reported by Wright. The spectroscopic data and specific rotation values of 10-epi-10-isothiocyanato-4-cadinene (6) and di-1,6-epi-10-isothiocyanato-4-cadinene (8) were also established through the syntheses of these diastereomers. Structure 6 has been reported as a natural product by Mitome et al., but the NMR data for the synthetic sample of 6 differ from those of the natural isolate.
authors.affiliation: Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Nishikawa
authors.forename: Taiki
authors.initials: T
authors.lastname: Umezawa
authors.forename: Mary J
authors.initials: MJ
authors.lastname: Garson
authors.forename: Fuyuhiko
authors.initials: F
authors.lastname: Matsuda
mesh_terms: D000818:Animals; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000081223:Polycyclic Sesquiterpenes; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C480379:10-isocyano-4-cadinene; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes