Reaction of Elemol with Acetic Acid/Perchloric Acid: Characterization of a Novel Oxide and (+)-β-Cyperone

The minor unidentified compounds of the acetic acid/perchloric acid dehydration of elemol (1) were fully characterized. The structure and relative configuration of the less polar fragrant compound 2, named elemoxide, was deduced by 1D‐ and 2D‐NMR data including C,C‐connectivity, NOE, and NOESY exper...

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Bibliographic Details
Published in:Helvetica chimica acta 2006-03, Vol.89 (3), p.496-501
Main Authors: Wahidulla, Solimabi, Govenkar, Mangala Babu, Paknikar, Sashikumar Keshav
Format: Article
Language:English
Subjects:
(+)-β-Cyperone
Dehydration
Elemenes
Elemol
Elemoxide
Perchloric acid
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Summary:The minor unidentified compounds of the acetic acid/perchloric acid dehydration of elemol (1) were fully characterized. The structure and relative configuration of the less polar fragrant compound 2, named elemoxide, was deduced by 1D‐ and 2D‐NMR data including C,C‐connectivity, NOE, and NOESY experiments. The absolute configuration was established as (3S,3aR,7aR)‐1,3,3a,4,7,7a‐hexahydro‐6‐isopropyl‐1,1,3,3a‐tetramethylisobenzofuran (2) on the basis of its preparation from elemol (1). (+)‐β‐cyperone (3), a known sesquiterpene, was also identified as a minor product of the reaction. A plausible mechanistic explanation for the formation of elemoxide (2) and (+)‐β‐cyperone (3) is presented.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200690050