“…l ~~ Aerial oxidation of 7-hydroxydehydronorglaucine [( 130), R = HI, in the presence of a platinum catalyst, yields the The pharmacological and physiological effects of apom ~r p h i n e , l ~~-l ~' of crebanine, 16k and of g l a ~c i n e ~~' have been Papaver sornniferurn has afforded the salutaridinol that is enzymatically converted into thebaine, and this alcohol has been shown by X-ray crystallographic studies to have the (7s) configuration (1 6 1) and not the (7R)-structure previously assigned to it. 180 Rearrangement of 3-0-trifluoromethylmethanesulfonylmorphine in methanesulfonic acid, followed by methylation with diazomethane, has afforded the apomorphine derivative 166), R1 = R2 = HI has been dehydrated with concomitant hydrolysis to the 14-alkenylcodeinone (1 67), reduced to the corresponding codeine, by previously well-documented methods.la5 The Diels-Alder addition of thebaine to the triterpene quinone (168) yielded the enolized adduct (169), which on thermal rearrangement yielded the naphthaquinol (170).1s6 The quaternary methosulfate [(171), R = MeSO,], obtained from the adduct of thebaine and 2-thiolen-4-one-1,ldioxide, on heating with silver oxide gives principally the enol methyl ether (172), whereas the corresponding iodide [( 171), R = I] gives mainly the methine base (173), with (172) as a minor product. ls7 X-Ray crystallographic studies of 6a-iododeoxnaltrexone [( 174), R1 = H, R2 = I] and the 6P-epimer [( 174 A new synthesis of 8-thebainone has been achieved from the quinone (195).…”