Published in

Elsevier, Tetrahedron: Asymmetry, 17-18(27), p. 829-833, 2016

DOI: 10.1016/j.tetasy.2016.07.007

Links

Tools

Export citation

Search in Google Scholar

5-epi-Incensole: synthesis, X-ray crystal structure and absolute configuration by means of ECD and VCD studies in solution and solid state

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

Full text: Unavailable

Green circle
Preprint: archiving allowed
Orange circle
Postprint: archiving restricted
Red circle
Published version: archiving forbidden
Data provided by SHERPA/RoMEO

Abstract

Incensole 1 and its acetate 2, found in incense, demonstrate interesting biological activities. Incensole acetate 2 was prepared on a large scale by employing the Paul and Jauch protocol from the crude extracts of Boswellia papyrifera Hochst. 5-epi-Incensole 3, obtained as colorless crystals, was prepared from incensole acetate via three steps; deacetylation, oxidation and reduction. The structure of 5-epi-incensole 3 was elucidated by means of spectroscopic data analysis, and the absolute configuration was established by single crystal X-ray analysis in combination with electronic and vibrational circular dichroism. In particular, the applicability of the solid-state ECD/TDDFT protocol to a compound with only two non-conjugated alkene chromophores was verified.