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Synthesis of galanthamine 329 Henry, T.A. and Sharp, T.M. (1930) Mercuration of some polyhydroxybenzaldehydes and their monomethyl ethers. Journal of the Chemical Society, 132 (2), 2279–2289. Henshilwood, J. and Johnson, N.B. (1996) Oxidative Process for Preparing Narwedine Derivative. International Patent Application No. WO 96 31,458. Holton, R.A. and Davis, R.G. (1977) Protection of phenols as methylthiomethyl ethers. Tetrahedron Letters, No. 6, 533–534. Holton, R.A., Sibi, M.P. and Murphy, W.S. (1988) Palladium-mediated biomimetic synthesis of narwedine. Journal of the American Chemical Society, 110 (1), 314–316. Ishizaki, M., Ozaki, K., Kanematsu, A., Isoda, T. and Hoshino, O. (1993) Synthetic approaches toward spiro[2,3-dihydro-4H-1-benzopyran-4,1′-cyclohexan]-2-one derivatives via radical reactions: total synthesis of (±)-lycoramine. Journal of Organic Chemistry, 58 (15), 3877–3885. Jackson, A.H. and Martin, J.A. (1966) Phenol oxidation. Part I. The synthesis of isoboldine and glaucine. Journal of the Chemical Society C, No. 22, 2061–2069. Jeffs, P.W. (1990) Amaryllidaceae alkaloids. Natural Product Reports, 7 (6), 549–556. Kametani, T. (1972a) Galanthamine Compounds. Japanese Patent No. 47-13,919 (Chemical Abstracts, 77, 48690). Kametani, T. (1972b) Galanthamine. Japanese Patent No. 47-46,079 (Chemical Abstracts, 78, 111577). Kametani, T., Seino, C., Yamaki, K., Shibuya, S., Fukumoto, K., Kigasawa, K., Satoh, F., Hiiragi, M. and Hayasaka, T. (1971a) Syntheses of heterocyclic compounds. CCCL XXXVI. Alternative total syntheses of galanthamine and N-benzylgalanthamine iodide. Journal of the Chemical Society (C), No. 6, 1043–1047. Kametani, T., Shishido, K., Hayashi, E., Seino, C., Kohno, T., Shibuya, Sh. and Fukumoto, K. (1971b) Syntheses of heterocyclic compounds. CCCXCVI. Alternative total synthesis of (±)-galanthamine. Journal of Organic Chemistry, 36 (9), 1295–1297. Kametani, T., Yamaki, K., Yagi, H. and Fukumoto, K. (1969a) Modified total synthesis of (±)-galanthamine through phenol oxidation. Journal of the Chemical Society (D), No. 8, 425–426. Kametani, T., Yamaki, K., Yagi, H. and Fukumoto, K. (1969b) Studies on the syntheses of heterocyclic compounds. CCCXV. Modified total synthesis of (±)-galanthamine through phenol oxidation. Journal of the Chemical Society (C), No. 18, 2602–2605. Kametani, T., Yamaki, K., Terui, T., Shibuya, Sh. and Fukumoto, K. (1972) Synthesis of heterocyclic compounds. CDLXVI. Synthesis of narwedine-type enones by photochemical cyclization. Journal of the Chemical Society Perkin Transactions I, No. 12, 1513–1516. Kametani, T., Yamaki, K. and Terui, T. (1973) Synthesis of analgetics. XXXV. Syntheses of heterocyclic compounds. DVII. Synthesis of (±)-N-norgalanthamine through phenol oxidation. Journal of Heterocyclic Chemistry, 10 (1), 35–37. Kita, Y., Arisawa, M., Gyoten, M., Nakajima, M., Hamada, R., Tohma, H. and Takada,T. (1998) Oxidative intramolecular phenolic coupling reaction induced by a hypervalent iodine (III) reagent: leading to galanthamine-type Amaryllidaceae alkaloids. Journal of Organic Chemistry, 63 (19), 6625–6633. Krikorian, D., Vlahov, R., Parushev, S., Chinova, M., Vlahov, I., Schafer, H.-J., Duddeck, H. and Shatzke, G. (1984) Synthesis of galanthamine: intramolecular para-ortho-coupling of diaryl ethers by anodic oxidation. Tetrahedron Letters, 25 (28), 2969–2972. Lewis, J.R. (1990) Amarylidaceae alkaloids. Natural Product Reports, 7 (6), 549–556. Lewis, J.R. (1997) Amaryllidaceae alkaloids. Natural Product Reports, 14 (3), 303–308. Martin, S.F. and Garrison, P.J. (1981) Total synthesis of racemic lycoramine. Journal of Organic Chemistry, 46 (17), 3567–3568. Martin, S.F. and Garrison, P.J. (1982) General methods for alkaloid synthesis. Total synthesis of racemic lycoramine. Journal of Organic Chemistry, 47 (8), 1516–1518. Mashkovsky, M.D. (1955) An influence of galanthamine on skeletal muscular sensitivity to acetylcholine. Farmakologia i toksikologia, 18 (4), 21–27 (in Russian).
330 V.N. Bulavka and O.N. Tolkachev Mashkovsky, M.D. and Kruglova-L’vova, R.P. (1951) About the pharmacology of new alkaloid galanthamine. Farmakologia i toksikologia, 14 (6), 27–30 (in Russian). Misaka, Y., Mizutani, T., Seukudo, M. and Uyeo, S. (1967) An improved synthesis of (±)-lycoramine. Chemical Communications, No. 24, 1258–1259. Misaka, Y., Mizutani, T., Seukudo, M. and Uyeo, Sh. (1968) The total synthesis of (±)-lycoramine. Chemical Communications, No. 23, 2954–2959. Missoum, A., Sinibaldi, M.-E., Vallee-Goyet, D. and Gramain, J.-C. (1997) Photochemical synthesis of spirocyclohexyl-isoquinolines, analogs of (±)-galanthamine and (±)-lycoramine. Synthetic Communications, 27 (3), 553–566. Moraes-Cerdeira, R.M., Burandt, C.L., Jr., Bastos, J.K., Nanayakkara, N.P.D., Mikell, J., Thurn, J. and McChesney, J.D. (1997) Evaluation of four Narcissus cultivars as potential sources for galanthamine production. Planta Medica, 63 (5), 472–474. Parker, K.A. and Kim, H.J. (1992) A short stereospecific synthesis of dl-lycoramine. Control of relative stereochemistry by dipole effects. Journal of Organic Chemistry, 57 (2), 752–755. Polt, R. (1996) Amaryllidaceae alkaloids with antitumor activity. Organic Synthesis: Theory Application, No. 3, 109–148. Proskurnina, N.F. and Yakovleva, A.P. (1952) On alkaloids of Galanthus woronowi. II. About isolation of new alkaloid. Zhurnal Obshchei Khimii, 22 (10), 1899–1902 (in Russian). Proskurnina, N.F. and Yakovleva, A.P. (1955) About alkaloids of Galanthus woronowi. III. About galanthamine structure. Zhurnal Obshchei Khimii, 25 (5), 1035–1039 (in Russian). Raiford, L.Ch. and Ravely, M.F. (1940) Action of bromine on vanillin, isovanillin, and some of their derivatives, and modifications of the directive influence of hydroxyl in these compounds. Journal of Organic Chemistry, 5 (1), 204–211. Sanchez, I.H., Soria, J.J., Lopez, F.J., Larraza, M.I. and Flores, H.J. (1984) Total synthesis of racemic lycoramine. Journal of Organic Chemistry, 49 (1), 157–163. Schultz, A.G., Yee, Y.K. and Berger, M.N. (1977) Total synthesis of dl-lycoramine. Journal of the American Chemical Society, 99 (24), 8065–8067. Schutte, H.R. (1969) Amaryllidaceenalkaloide. In: K. Mothes and H.R. Schutte, (eds.), Biosynthese der Alkaloide, VEB Deutscher Verlag der Wissenschaften, Berlin, pp. 420–438. Shieh, W.-Ch. and Carlson, J.A. (1994) Asymmetric transformation of either enantiomer of narwedine via total spontaneous resolution process, a concise solution to the synthesis of (–)-galanthamine. Journal of Organic Chemistry, 59 (18), 5463–5465. Shieh, W.-Ch. and Carlson, J.A. (1995) Method of Manufacture of (–)-Galanthamine in High Yield and Purity Substantially Free of Epigalanthamine. US Patent No. 5-428-159 (Chemical Abstracts, 123, 112051). Shimizu, K., Tomioka, K., Yamada, S. and Koga, K. (1977) A biogenetic-type asymmetric synthesis of optically active Amaryllidaceae alkaloids: (+)- and (–)-galanthamine from L-tyrosine. Heterocycles, 8, 277–282. Shimizu, K., Tomioka, K., Yamada, S. and Koga, K. (1978) Stereochemical studies. LIV. A biogenetic-type asymmetric synthesis of optically active galanthamine from L-tyrosine. Chemical and Pharmaceutical Bulletin, 26 (12), 3765–3771. Szewczyk, J., Levin, A.H. and Carroll, F.I. (1988) Improved synthesis of galanthamine. Journal of Heterocyclic Chemistry, 25 (6), 1809–1811. Szewczyk, J., Wilson, J.W., Levin, A.H. and Carroll, F.I. (1995) Facile synthesis of (+)- and (–)- galanthamine. Journal of Heterocyclic Chemistry, 32 (1), 195–199. Thal, C., Guillou, C., Mary, A., Renko, D., Potier, P. and Christen, Y. (1997) Preparation and Pharmaceutical Compositions of Galanthamine Derivatives. International Patent Application No. WO 97 3,987. Tiffin, P.D., Fraser, N. and David, A. (1997) Galanthamine Derivatives and Process for their Preparation. International Patent Application No. WO 97 11,077 (Chemical Abstracts, 126, 264239). Vaghani, D.D, and Merchant, J.R. (1961) Reactions of nitriles. Part I. Condensation of methyleneaminonitrile with aldehydes. Journal of the Chemical Society, No. 3, 1066–1068.
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Narcissus and Daffodil
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Narcissus and Daffodil The genus Na
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Contents Preface to the series vii
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Preface to the series There is incr
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Preface My interest in flower-bulb
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Acknowledgements I would like to th
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Gordon R. Hanks Crop and Weed Scien
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Figures 1.1 The effect of bulb stor
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Figures/Plates xvii 7.8 Accumulatio
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Figures/Plates of different segment
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2 G.R. Hanks Information about the
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4 G.R. Hanks (1999), and the polysa
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3 2 4 1 1 3 2 4 5 Flowering in 1976
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8 G.R. Hanks Figure 1.6 Diagrammati
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10 G.R. Hanks (Rees, 1969). When fl
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12 G.R. Hanks Figure 1.8 The relati
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14 G.R. Hanks root system of commer
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16 G.R. Hanks Cremer, M.C., Beijer,
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18 G.R. Hanks Roh, S.M. and Lee, J.
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20 A.C. Dweck Figure 2.1 The narcis
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22 A.C. Dweck Julians Hertfordshire
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24 A.C. Dweck Herefordshire, if daf
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26 A.C. Dweck the basis of an ancie
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28 A.C. Dweck Britten, J. and Holla
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3 Classification of the genus Narci
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(1) (2) (3)
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34 B. Mathew d. Section Jonquillae
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36 B. Mathew N. cyclamineus DC. Flo
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38 B. Mathew 1c. Section Ganymedes
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40 B. Mathew umbel, fragrant; peria
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42 B. Mathew recognition whatsoever
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44 B. Mathew Note: N. elegans shows
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46 B. Mathew ssp. praecox Gatt. and
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(1) (2) (3) (4)
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50 B. Mathew Table 3.1 Horticultura
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52 B. Mathew RHS (1958) The Classif
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54 G.R. Hanks grown for galanthamin
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56 G.R. Hanks such as drying stores
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Table 4.4 Areas of Narcissus cultiv
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60 G.R. Hanks Following planting in
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62 G.R. Hanks lost, resulting in th
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64 G.R. Hanks pathogen-tested nucle
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Figure 4.1 Mean monthly weather dat
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68 G.R. Hanks (as well as natural e
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70 G.R. Hanks compaction and its ef
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72 G.R. Hanks bulbs with base rot)
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74 G.R. Hanks Figure 4.3 Modern fro
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76 G.R. Hanks caution. Higher rates
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78 G.R. Hanks can also be prevented
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80 G.R. Hanks Figure 4.4 A typical
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82 G.R. Hanks Planting date The pra
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84 G.R. Hanks Hanks and Jones, 1986
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86 G.R. Hanks On sloping sites, gro
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88 G.R. Hanks Insecticide and nemat
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90 G.R. Hanks bulb growth, especial
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92 G.R. Hanks Figure 4.7 Changes in
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94 G.R. Hanks methods have been tes
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96 G.R. Hanks the boxes, exiting at
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98 G.R. Hanks usually collected in
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100 G.R. Hanks respond to ethylene
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102 G.R. Hanks using thiabendazole
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104 G.R. Hanks required for the eff
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106 G.R. Hanks and cross-cutting, s
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108 G.R. Hanks In practice, moulds
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110 G.R. Hanks that, with enterpris
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112 G.R. Hanks Balatková, V., Tupy
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114 G.R. Hanks (Narcissus pseudonar
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116 G.R. Hanks Flint, G.J. (1983) E
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118 G.R. Hanks Hanks, G.R. and Rees
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120 G.R. Hanks Khatib, K. al (1996)
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122 G.R. Hanks Luyten, I. (1935) Ve
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124 G.R. Hanks O’Neill, T.M., Man
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126 G.R. Hanks Ruamrungsri, S., Rua
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128 G.R. Hanks Thompson, P.A. (1977
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130 G.R. Hanks Williams, M. (1996)
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132 J.B. Briggs Table 5.1 Typical g
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134 J.B. Briggs Table 5.3 Actual gr
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136 J.B. Briggs Table 5.4 Actual co
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138 J.B. Briggs Table 5.5 Capital c
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140 J.B. Briggs ADAS (1987a) Narcis
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142 J. Bastida and F. Viladomat Fig
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Table 6.1 Narcissus alkaloid struct
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Table 6.1b Continued Alkaloid name
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Table 6.1d Tazettine type O O R1 R2
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Table 6.1f Continued MeO Alkaloid n
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Table 6.2 Continued Species* Alkalo
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162 J. Bastida and F. Viladomat Tab
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Table 6.3 Continued Alkaloid* Formu
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Table 6.3 Continued Alkaloid* Formu
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176 J. Bastida and F. Viladomat Tab
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178 J. Bastida and F. Viladomat Cri
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180 J. Bastida and F. Viladomat It
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184 J. Bastida and F. Viladomat is
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186 J. Bastida and F. Viladomat and
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Table 6.4 Continued Alkaloid Activi
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196 J. Bastida and F. Viladomat tac
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198 J. Bastida and F. Viladomat Ang
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200 J. Bastida and F. Viladomat Boi
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202 J. Bastida and F. Viladomat lyc
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204 J. Bastida and F. Viladomat Fug
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206 J. Bastida and F. Viladomat Han
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208 J. Bastida and F. Viladomat Kin
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210 J. Bastida and F. Viladomat of
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212 J. Bastida and F. Viladomat Sp
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214 J. Bastida and F. Viladomat Wil
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216 C. Codina and, consequently, hi
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218 C. Codina easily lost on transf
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220 C. Codina they might be more su
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222 C. Codina µ g/g FW µ g/g FW 3
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224 C. Codina Kinetin As observed i
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226 C. Codina Table 7.3 Total produ
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228 C. Codina Accumulation of alkal
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230 C. Codina Accumulation of alkal
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232 C. Codina Effect on growth and
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234 C. Codina mg/g DW mg/g DW 0.90
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236 C. Codina mg/g DW mg/g DW 1.4 1
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238 C. Codina mg/g DW mg/g DW 1.5 1
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240 C. Codina Hanks, G.R. and Jones
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8 Narcissus and other Amaryllidacea
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244 O.A. Cherkasov and O.N. Tolkach
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9 Studies on galanthamine extractio
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258 M. Kreh Table 9.1 Results of ga
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260 M. Kreh relation to the qualita
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262 M. Kreh Figure 9.3 Galanthamine
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264 M. Kreh 2.0 flower 2 1 3 4 0 10
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266 M. Kreh • High purity of the
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268 M. Kreh fraction of Narcissus
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H O MeO O MeO H H HO H (1) (3) + 2
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272 M. Kreh Gorinova, N.I., Atanass
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274 R.M. Moraes (Katz and Taneck, 1
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276 R.M. Moraes bulbs of many Narci
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Page 305 and 306: 284 R.M. Moraes Kosley, R.W., Jr.,
Page 307 and 308: 11 Extraction and quantitative anal
Page 309 and 310: 288 N.P.D. Nanayakkara and J.K. Bas
Page 317 and 318: Table 11.1 GC and HPLC procedures f
Page 319 and 320: Table 11.1 Continued References Det
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Page 353 and 354: 13 Compounds from the genus Narciss
Page 355 and 356: 334 D. Brown with neostigmine the a
Page 357 and 358: 336 D. Brown Absorption Galanthamin
Page 359 and 360: 338 D. Brown Metabolism and excreti
Page 361 and 362: 340 D. Brown were internationally i
Page 363 and 364: 342 D. Brown cortex and hippocampus
Page 365 and 366: 344 D. Brown reasoned that the effi
Page 367 and 368: 346 D. Brown Galanthamine causes br
Page 369 and 370: 348 D. Brown (1994) go on to mentio
Page 371 and 372: 350 D. Brown (Punto Toro and Rift V
Page 373 and 374: 352 D. Brown Furusawa, E., Lum, M.K
Page 375 and 376: 354 D. Brown Snorrason, E. and Stef
Page 377 and 378: 356 D. Brown examination of a brain
Page 379 and 380: 358 D. Brown A successful cholinerg
Page 381 and 382: Table 14.2 Summary of human trials
Page 383 and 384: 362 D. Brown statistically signific
Page 385 and 386: 364 D. Brown ( Jann, 1998); see Tab
Page 387 and 388: 366 D. Brown REFERENCES Bartus, B.T
Page 389 and 390: 368 D. Brown Wilcock, G.K., Scott,
Page 391 and 392: 370 K. Ingkaninan, H. Irth and R. V
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16 Narcissus lectins Els J.M. Van D
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382 E.J.M. Van Damme and W.J. Peuma
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17 Narcissus in perfumery HISTORY C
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394 C. Remy Figure 17.2 Flower coll
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Figure 17.3 Narcissus flowers sprea
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398 C. Remy CONCLUSION The use of n
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400 C.G. Julian and P.W. Bowers Fig
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406 C.G. Julian and P.W. Bowers sym
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19 Review of pharmaceutical patents
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410 J.R. Murray to certain RNA viru
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412 J.R. Murray occurs in a two-pha
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414 J.R. Murray cognitive function
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416 J.R. Murray given at a time bet
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418 J.R. Murray Hofmannor, D., Mosc
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420 Index Backache, 403 Bacterial d
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422 Index Divisions (classification
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424 Index Leaf numbers, 11 Leaf sco
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426 Index Poet’s cultivars, 34 Po
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428 Index Subgenus (taxonomy); Ajax
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