Ocobotrine

In the trans-B/c-8,14-dihydromorphinandienone, ocobotrine [182], (129) there is close approach of the 4-hydroxyl group and the olefinic... 

Fourteen alkaloids were isolated from extracts of the whole plant of ThaUctrum fauriei Hayata, among which were seven alkaloids of novel structure including three aporphines (3-0-demethyloconovine, faurine, and O-methylfaurine), three aporphine-benzylisoquinoline dimers (fauridine, faurithaline, and 3-methoxyfaurithaline), and one aporphine-pavine dimer (fauripavine). Alkaloids of previously established structure that were isolated and identified included five aporphines (corydine, isocorydine, isooconovine, oconovine, and thalisopynine), and two morphinans (ocobotrine and pallidine). 

Seven alkaloids were isolated from extracts of the roots of ThaUctrum foetidum L. including one new alkaloid, the bismorphinan bisocobotrine. Alkaloids of hitherto established structures that were isolated included one benzylisoquinoline (reticuline), two morphinans (ocobotrine and sinoacutine), and three bisbenzylisoquinolines (thalibrine, thalidasine, and thalirugosidine). 

Nor-oripavine has been isolated as the new base oripavidine from P. orientate. Its structure has been confirmed by Eschweiler methylation to oripavine followed by O-methylation to thebaine with diazomethane.Two other new bases, ocobotrine (141) and 14-ep/-sinomenine (142), have been isolated, together with sinoacutine and pallidine, from Ocotea brachybotra. ... 

The variety of morphinan alkaloids of this class is illustrated in Fig. 9, by the unnatural (-)-sinomeninone, its two enol ethers (Minamikawa and Brossi 1978) and ocobotrine and 14-eposinomenine, alkaloids of the B/C transseries (Vecchietti et al. 1976). This group of alkaloids will undoubtedly further increase and sooner or later selected representatives will become available for pharmacological screening. 

Vecchietti y, Casagrande C, Gerrari G (1976) Ocobotrine and 14-episinomenine, new trans-mor-phinane alkaloids ofOcotea brachybotra. Tetrahedron Lett 1631-1633 Weller DD, Rapoport H (1976) A practical synthesis of codeine from dihydrothebainone. J Med Chem 19 1171-1175... 

---