✍ Scribed by Solimabi Wahidulla; Mangala Babu Govenkar; Sashikumar Keshav Paknikar
No coin nor oath required. For personal study only.
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.
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