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Reaction of Elemol with Acetic Acid/Perchloric Acid: Characterization of a Novel Oxide and (+)‐ β ‐Cyperone
Author(s) -
Wahidulla Solimabi,
Govenkar Mangala Babu,
Paknikar Sashikumar Keshav
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690050
Subject(s) - chemistry , acetic acid , sesquiterpene , perchloric acid , stereochemistry , isopropyl , absolute configuration , organic chemistry
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 (3 S ,3a R ,7a R )‐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.