Confirmation of the configuration of 10-isothiocyanato-4-cadinene diastereomers through synthesis

J Nat Prod. 2012 Dec 28;75(12):2232-5. doi: 10.1021/np300439e. Epub 2012 Nov 19.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Polycyclic Sesquiterpenes
  • Porifera / chemistry
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry*
  • Stereoisomerism

Substances

  • 10-isocyano-4-cadinene
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes