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Renewed efforts were made to gain access to the long neglected morphine fragment 2d, trans-1,3,4,5,6,7,8,8a-octahydro-2-methyl-4a-phenylisoquinolin-6-ol. Previous efforts by McElvain involved an unsuccessful attempt at the conjugate addition of phenylmagnesium bromide to the enone 17, 1,3,4,7,8,8a-hexahydro-2-methylisoquinolin-6-one. Our first attempt involved intramolecular alkylation of the ketal 8b, which was not successful. Use of diphenylcopper lithium, however, enabled us to achieve conjugate addition to the enone 17, giving stereospecifically the cis ketone 18, l,3,4,7,8,8a-hexahydro-2-methyl-4a-phenylisoquinolin-6-one, whose structure was confirmed by X-ray analysis of the methobromide. The stereochemistry of reduction and methyllithium addition to this ketone 18 is discussed.

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Registry No. -2-Fluoro-2,2-dinitroethanol, 17003-75-7; (2-fluoro-2,2-dinitroethyl) methylamine, ; (2-fluoro-2,2-dinitroethyl)dimethylamine, ; (2fhioro-2,2-dinitroethyl) aminoacetic acid, 30409-37-1; ethyl 2-fluoro-2,2-dinitroethylaminoacetate, 30409-38-2; (2-fluoro-2,2-dinitroethyl) aminoacetaldehyde diethyl acetal, 30409-39-3; (2-fluoro-2,2-dinitroethyl)aminosuccinic acid, 30476-99-4; 2-(2-fluoro-2,2-dini-troethylamino) ethanol, 30409-40-6; A-(2-fluoro-2,2dinitroethyl)allylamine, 30409-41-7; Ar,A'-bis(2-fluoro-2.2-dinitroethyl)allylamine, 30409-42-8; AT,A7'-bis(2fluor o -2,2 -dinitroethyl) -Ar,A"'-bis (carbethoxymethyl)methylenediamine, 29925-43-7; Ar,Ar'-bis(2-fluoro-2.2-dinitroethyl)hydrazine, 30409-44-0; ethyl (2-fluoro-2.2-dinitroethyl) carbamate, 30409-45-1; methyl (2fluoro-2,2-dinitroethyl) carbamate, 30409-46-2; isopropyl (2-fluoro-2,2-dinitroethyl) carbamate, 30409-47-3; 2-fluoro-2,2-dinitroethylammonium bisulfate, 30409-48-4.