Morphine alkaloids, 2, 1 , 2, 161 part

Morphine alkaloids. Part 116. Synthesis of N-demethyl-N-substituted dihydroisomorphine and dihydroisocodeine derivatives... 

Morphine alkaloids. Part 114. A stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines... 

The facts that the degradation of the morphine alkaloids to fully aromatic phenanthrene derivatives is always accompanied by loss of the whole of the basic side-chain, and that loss of the latter is never observed independently of formation of such an aromatic derivative, led Gulland and Robinson [1, 118] to perceive that the nitrogen-containing side-chain must be so located that its extrusion is a necessary part of aromatization. The only positions for the attachment of the carbon end of the side-chain on this assumption are C-13 and C-14 of the phenanthrene skeleton, and the formulae [cxi] for codeine and [cxn] for thebaine were accordingly advanced [1], later being modified to [cxm] and [oxiv] respectively [118]. Such formulations allow the construction of plausible mechanisms for the degradation of the morphine alkaloids to phenanthrene derivatives. 

In this monograph each chapter is intended to be as far as possible a complete account of one section of the work, even though this has necessitated the duplication of certain parts. It is hoped that all papers relating to the chemistry of the morphine alkaloids published before 1 February 1953 are referred to in the monograph. 

FIGURE 7.3 A structure of enkephalins (Met and Leu). The broken line indicates the alkaloid part (a derivative of tyramine) of the enkaphelins. This structural element change of -NHj group -NCHj group is also found in natural morphine. 

Battersby, A. R. and D. M. Foulkes, Alkaloid biosynthesis. Part VIII Use of optically active precursors for investigations on biosynthesis of morphine alkaloids, J. Chem. Soc., 3323-3332 (1965). 

Beyerman HC, Lie TS, Maat L, Buurman E, Bijsterveld EJM, Sianige HIM (1976a) A convenient synthesis of codeine and morphine. Reel Trav Chim Pays-Bas Belg 95(l) 24-25 Beyerman HC, Bommel L van, Maat L, Olieman C (1976b) Reel Trav Chim Pays-Bas Belg 95 312 Beyerman HC, Leeuwen FF van. Lie TS, Maat L, Olieman C (1976c) Chemistry of opium alkaloids, part VI, A practical technique for laboratory Birch reductions. Reel Trav Chim Pays-Bas Belg 95(10) 238-240... 

Lie TS et al. (1978a) Chemistry of opium alkaloids, part XI. Synthesis of racemic and chiral codeine and morphine via the dihydrothebainones. Reel Trav Chim Pays-Bas Belg 98 419-420... 

Barton DHR, Bhakuni DS, James R, Kirby GW (1967) Phenol oxidation and biosynthesis, part XII. Stereochemical studies related to the biosynthesis of the morphine alkaloids. J Chem Soc (0 128 132... 

Holmes HL (1952) The morphine alkaloids. In Manske RHF, Holmes HL (eds) The alkaloids, vol II, chap 8, parts 1,2. Academic, London New York Hughes J, Smith TW, Kosterlitz HW, Fothergill LA, Morgan BA, Morris HK (1975) Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature (London) 258 577-579... 

Leimgruber W, Mohasci E (1972) Derivatives of Morphinan. US Pat 3634429 Lie TS, Maat L, Beyerman HC (1979) Chemistry of opium alkaloids, part XI. Synthesis of racemic and chiral codeine and morphine via the dihydrothebainones. Reel Trav Chim Pays-Bas Belg 98(6) 419-420 and references dted therein MacKay M, Hodgkin DC (1955) A crystallographic examination of the structure of morphine. JChem Spe 3261-3267... 

Battersby AR, Evans GW, Martin RO, Warren ME Jr, Rapoport H (1965b) Configuration of re-ticuline in the opium poppy. Tetrahedron Lett 1275-1278 Battersby AR, Martin JA, Brochmann-Hanssen E (1967) Alkaloid biosynthesis, part X. Terminal steps in the biosynthesis of the morphine alkaloids. J Chem Soc (C) 1785-1788 Blaschke G, Parker HI, Rapoport H (1967) Codeinone as the intermediate in the biosynthetic conversion of thebaine to codeine. J Am Chem Soc 89 1540-1541 Borkowski PR, Horn JS, Rapoport H (1978) Role of 1,2-dehydroreticulinium ion in the biosynthetic conversion of reticuline to thebaine. J Am Chem Soc 100 276-281 Brochmann-Hanssen E (1984) A second pathway for the terminal steps in the biosynthesis of morphine. Planta Med 51 343-345... 

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