Opium, alkaloids dihydrocodeinone

Rice, K.C. (1980) Synthetic Opium Alkaloids and Derivatives. A Short Total Synthesis of (ib)-Dihydrothebainone, ( )-Dihydrocodeinone, and ( )-Nordihydrocodemone as an Approach to a Practical Synthesis of Morphine, Codeine, and Congeners. Journal of Organic Chemistry, 45, 3135-3137. 

Hong, C.Y, Kado, N., Overman, L.E. (1993) Asymmetric Synthesis of Either Enantiomer of Opium Alkaloids and Morphinans. Total Synthesis of (—)- and (-f)-Dihydrocodeinone and (—)- and (-F)-Morphine. Journal of the American Chemical Society, 115, 11028-11029. 

Hydrocodone, 4,5-Epoxy-3-methoxy- 17-methvt-morphinan-6-one dihydrocodeinone Bekadid Dicodid. C,H31NOj mol wt 299.36. C 72.21%, H 7-07%, N 4.68%, O [6,03%. Prepn by hydrogenation of codeinone Mannich, Lowenheim, Arch. Pharm. 258, 295 (1920) by oxidation of dihydrocodeine, Ger. pat. 415,097 (1925 to E. Merck), Frdl. 15, 1518 (1925-1927) by catalytic rearrangement of codeine Ger. pet. 623,821. Industrial prepn from dihydrocodeine Pfister. Tishler, U.S. pal, 2,715,626 (1955 to Merck Co-)-Toxicity data Eddy, Reid, J. Pharmacol. Exp. Ther. 52,468 (1934). Review Small. Lutz. "Chemistry of the Opium Alkaloids, Suppl. No. 103, Public Health Reports, Washington (1932). 

Rice KC (1980) Synthetic opium-alkaloids and derivatives - a short total synthesis of (-1-/—)-dihydrothebainone, (+/—)-dihydrocodeinone, and (-f/—)-nordihydrocodeinone as an approach to a practical synthesis of morphine, codeine, and congeners. J Org Chem... 

Hong CY, Kado N, Overman LE (1993) Asymmetric-synthesis of either enantiomer of opium-alkaloids and morphinans - total synthesis of (—)-dihydrocodeinone and (-1-)-dihydrocodeinone and (—)-morphine and (+)-morphine. J Am Chem Soc 115 11028-11029 Mulzer J, Dumer G, Trauner D (1996) Formal total synthesis of (—)-morphine by cuprate conjugate addition. Angew Chem hit Ed 35 2830-2832... 

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