The Veratrum Alkamines 



311 



methyl substitution in the cyclopentene ring of the dehydrogenatioE 

 product VIII6, but a more cogent argument evolved from the qua- 

 ternary base nature of the intermediates Xlla and XII6 (originally 

 regarded as the normal 18-O-tosylate and 18-iodide 5 in the sequence 

 by which isorubijervine was converted to solanidine; 5 7 clearly, of the 

 methyl carbons in the vicinity of the basic group only C-18 fulfills the 

 steric requirements for facile formation of a bond to the nitrogen atom. 



IX (R = H) Solanidine 

 X |R = ---OH) Rubijervine 



CH..OH 



XI Isorubijervine 



Ci.iH.mO 



Na, C,H s OH 



IX 



Xlla (X = p-CH :i -C 6 H 4 -S0 3 ) 

 Xllb (X = I| 



With the presence of a normal steroidal nucleus in these two bases 

 assured, it was only natural that in the tentative expressions which 

 had meanwhile been proposed for jervine 8 and cevine 9 these alkamines 

 were also accorded the normal structure. Implicit in these formula- 

 tions was the assumption that the "abnormal" fluorene-like hydrocar- 

 bons formed from these bases in the selenium dehydrogenation were 

 probably artifacts resulting from skeletal rearrangements such as some- 

 times occur in this high temperature reaction. That, to the contrary, 

 these products accurately mirror the original ring system was first 



