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.
5-epi-Incensole: synthesis, X-ray crystal structure and absolute configuration by means of ECD and VCD studies in solution and solid state
PESCITELLI, GENNARO;
2016-01-01
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.File | Dimensione | Formato | |
---|---|---|---|
incensole.pdf
Open Access dal 01/11/2018
Tipologia:
Documento in Post-print
Licenza:
Creative commons
Dimensione
370.23 kB
Formato
Adobe PDF
|
370.23 kB | Adobe PDF | Visualizza/Apri |
1-s2.0-S095741661630163X-main.pdf
non disponibili
Tipologia:
Versione finale editoriale
Licenza:
NON PUBBLICO - accesso privato/ristretto
Dimensione
1.16 MB
Formato
Adobe PDF
|
1.16 MB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.