Incensfuran: isolation, X-ray crystal structure and absolute configuration by means of chiroptical studies in solution and solid state

TitleIncensfuran: isolation, X-ray crystal structure and absolute configuration by means of chiroptical studies in solution and solid state
Publication TypeJournal Article
Year of Publication2017
AuthorsRehman N.U, Hussain H., Al-Shidhani S., Avula S.K, Abbas G., Anwar M.U, Gorecki M., Pescitelli G., Al-Harrasi A.
JournalRsc Advances
Volume7
Pagination42357-42362
Date Published2017/08
Type of ArticleArticle
ISBN Number2046-2069
Accession NumberWOS:000409147500045
Keywordscircular-dichroism; derivatives; ecd; spectra
Abstract

A new cembrane diterpene named incensfuran (1), biogenetically derived from incensole (2), was isolated from crude extracts of the Boswellia papyrifera Hochst. The structure of incensfuran (1) was elucidated by 1D and 2D NMR study, and its absolute configuration was determined by single crystal X-ray diffraction analysis and electronic and vibrational circular dichroism spectroscopy (ECD, VCD). Moreover semisynthesis of incensfuran (1) was achieved after treatment of incensole (2) with BF3 center dot OEt2. In addition epoxidation of incensfuran (1) provided expoxide analog 3 with 80% yield.

DOI10.1039/c7ra07351h
Short TitleRSC Adv.
Student Publication: 
No
Research Topics: