Terpenoids. XXVIII. Acorane type sesquiterpenoids from juniperus rigida and hypothesis for the formation of new tricarbocyclic sesquiterpenoids
✍ Scribed by B. Tomita; T. Isono; Y. Hirose
- Publisher
- Elsevier Science
- Year
- 1970
- Tongue
- French
- Weight
- 137 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
In the preceding papers, l-248 have rep orted on the stereostructures of acoradiene (1) and acorenol (3) isolated from the wood of Juniper-us rigida and their transformation into (-)-a-cedrene. In this paper we wish to propose the revision of the name from acoradiene and acorenol to a-acoradiene3)and a-acorenol, respectively , and describe in continuation the structures of further isolated acorane-type sesquiterpenes; F-acoradiene, p-acorenol, Y-acoradiene, and 6-acoradiene. j-Acoradiene(2) A new hydrocarbon, C15H24, m/e M+ 204, Cal, f23', had a terminal double bond; yiaFid1640 and 890 cm-'; 6(100 MC, CC14) 4.60, 4.75(each lH, br s), a trisubstituted double bond; 805 cm-l; b 5.25(1H, m), a secondary methyl group; 6 0.87(3H, d, J=7 cps), and two allylic methyl groups; 6 1.60, 1.74(each 3H). On hydrogenation(Pt02/ AcOH) it gave a mixture of two tetrahydro derivatives, [a], -58-(mixture)t)both of which were identical with respective acoranes, [a] 4) D -45'(mixture), synthesized from a-acoradiene by comparison of their IR spectra and Rts in GLC.