Hexahydro-fluorene

Scheme 2 Simplified catalytic cycles leading to the formation of 2,6-di-n-propyl-l,T-(l,2-ethynediyl)bisbenzene and E-9- [ 1 -(2",6"-di- i-propylphenyl)- 1-phenylmethylene] -1,2,3,4,4a,-9a-hexahydro- 1,4-methano- IfJ-fluorene...

The above-described thermal degradations afford an insight into the molecule of cevine that centers about the nitrogen atom. The formation of the typical 2-ethyl-5-methylpyridine as w ell as its hexahydro derivative indicate that the nitrogen-containing moiety of cevine is closely related to the analogous portion of other Solanum and Veratrum alkaloids. Less easily interpretable is the formation of 1,2-benzohydrindane as well as the numerous fluorene derivatives. It is nevertheless not improbable that the carbon skeleton of cevine is similar to that of veratramine and of jervine. 

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