Himachalanes

New additions to the himachalane class include (213)—(215) Cineraria gei-foliaf and podocephalol (216) Lasianthaea podocephala) Piers et ahave now utilized the Cope rearrangement of /S-(2-vinylcyclopropyl)-a,jS-unsaturated ketones for the construction of jS-himachalene (217) (Scheme 34). 

Two new himachalane sesquiterpenoids, centdarol (194) and isocentdarol (195), have been isolated from the wood of Cedrus deodora and assigned structures (194) and (195) on the basis of their chemical and spectroscopic properties. 

Bonds between C-1 and C-6 as well as C-1 and C-11 formally convert famesane into the bicyclic skeleton of himachalane with the numbering system adopted from that of famesane. Several himachalanes such as a-himachalene and himachalol are constituents of the oil of cedar wood from Cedrus deodara (Pinaceae). 

Compounds with the himachalane skeleton were first isolated from the essential oil of Cedrus deodara, and include a-himachalene (341), himachalol (342) and oxidohimachalene (343) (34, 220, 346). Many related compounds are now known to occur in nature the keto diol ester 344 from roots of Senecio deltoideus... 

Along with longifolane- and longipinane-types sesquiterpenes, (-h)-a-himachalene (436), (—)-P-himachalene (437) and (-h)-y-himachalene (438) have been isolated from Scapania undulata (2, 223). All himachalanes isolated are antipodal to those obtained from higher plants. 

Chart 20. Himachalanes, longifolanes, longipinanes, and sativanes found in the Hepaticae... 

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