Structure and synthesis of a new ketone from Cedrus species; some new constituents of C. atlantica Manet
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 15,p. 1502-1506
- https://doi.org/10.1039/p19750001502
Abstract
Details are given of the structure and two syntheses of a new C12 ketone [4-(4-methylcyclohex-3-enyl)pent-3-en-2-one] isolated from the essential oils of Cedrus atlantica Manet and C. deodara Loud. The absolute configuration of the C12 ketone follows from the synthesis of the natural enantiomorph by acetylation of (+)-p-mentha-1,8-diene at C-9. The presence of deodarone [2,2,6-trimethyl-6-(4-methylcyclohex-3-enyl)tetrahydro-4-pyrone] in Cedrus atlantica is reported for the first time and clear proof of its structure is presented by dehydration to α-atlantone [2-methyl-6-(4-methylcyclohex-3-enyl)hepta-2,5-dien-4-one]. Other new constituents of Cedrus atlantica include α-caryophyllene alcohol, obtained for the first time as a natural product, epi-β-cubenol, α-ionone, and two new epoxides, epoxy-β-himachalene and epi-epoxy-β-himachalene (2,4a,5,6,7,8,9,9a-octahydro-3,5,5,9-tetramethyl-9,9a-epoxy-1H-benzocycloheptene).Keywords
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