Chemistry 165 



opposite direction to expand the central ring of 2:3: l:7-tctramethoxy- 

 10-niethvlj)hcnanthrenc (IX). Hiis took ad\antage of the known 

 reactivity of the 9:10-double bond in phenanthicnes and hvdroxyla- 

 tion, scission, and renewed cyclization led to an unsatinated ketone 

 (X) identical with the one produced, as already mentioned, by oxida- 

 tion of deaminocolchinol methyl ether. Moreover, by applying the 

 same series of reactions to 2:3:4: 7-tetra-methoxy-9-methylphen- 

 anthrene (XI) Cook, Jack, and Loudon-' obtained an isomeric tm- 

 saturated ketone (XII) . This was reduced to the saturated ketone 

 (XIII) and thence by oxiniation and rcneAsed reduction was con- 

 verted to tlie (rt) -amine (X\' I) . Optical resolution of this amine, 

 through its salts Avith (-]-) -6:6'-dinitrodiphenic acid, afforded the 

 ( — ) -base and hence the ( — ) -acetyle derivati\e and these resj^ectively 

 were identical with colchinol methyl ether and its A'-acetvl derivative 



^^o 



/\ 



OMe 



(XI) 



(XII) 



MeO 



MeO 



\U' 



(XIII) 



OMe 



(XIV) 



as obtained by degradation of colchicine. -"^ By a different loute start- 

 ing from the 9-monoxime of 2:3:4:7-tetramethoxyphenanthraquinone 

 Rapojjoii, Williams, and Cisney also synthesized the (h=) -amine 

 (XIV) and showed it to be identical witli i acemized colchinol mcthvl 

 ether.2» 



A second series of degradati(;n prcxiucts has a bearing on the struc- 

 ture of ring B. \\^indausi'' found that A"-benzoyltrimethylcolchicinic 



