Narcissus and Daffodil

More documents

Recommendations

Info

OH O MeO PhCH 2O CHO O PhCH 2O OH HO N OCH 2Ph NMe OMe PhCH 2O PhCH 2O Synthesis of galanthamine 307 on hydrolysis produced (±)-26 (98%). (±)-25 on keeping at 25 °C in the presence of Ph 3 P (14 h) yielded (±)-2 (51%). Thus the total yield of (±)-2 was 43.6%. Hence, the concept of using metal-substituted substrate-induced o-diphenol oxidation in galanthamine synthesis was successful. However, the use of toxic, expensive and scarce compounds means that the scheme is unsuitable for large-scale application. Synthesis of galanthamine and N-norgalanthamine via belladine-derived amide oxidation OH Me N MeO OCH 2Ph A significant achievement in the synthesis of 1 was found in the work of Kametani et al., 1969a,b and Kametani, 1972a, shown on Figure 12.4. 5-Benzyloxy-2-bromo- NMe OCH 2Ph 7 8 9 10 11 OH OMe OH MeO OCH 2Ph 12 13 14 O O HO HO OCH 2Ph Cl Me NH NMe 15 16 6 O OMe Figure 12.2 Synthesis of narwedine (2) via N,O-dimethylnorbelladine (6) (Barton and Kirby, 1960, 1962). 2
308 V.N. Bulavka and O.N. Tolkachev MeO CHO 17 CHO O OMe O OMe MeS MeS OH MeO O SMe 18 19 20 21 MeS Me HO NH 2 HO HO O O + O N OH O OMe MeS 2 O 25 26 4-methoxy-benzaldehyde (29) was oxidised with silver oxide into the corresponding acid 30 (89%), which was then transformed into the acid chloride 31 (52%). The coupling component 28 was obtained from 4-benzyloxyphenylacetic acid (10) via the acid chloride 11, N-methyl acetamide (27) (91%) and final reduction to 28 NMe HO OMe N Me N OMe 22 23 24 NMe PdCl SMe O O HO Cl Pd SMe O O OH NH NMe PdCl SMe Figure 12.3 Synthesis of narwedine (2) via palladium-containing intermediate (24) (Holton et al., 1988).
Page 2 and 3:
Narcissus and Daffodil
Page 4 and 5:
Narcissus and Daffodil The genus Na
Page 6 and 7:
Contents Preface to the series vii
Page 8 and 9:
Preface to the series There is incr
Page 10 and 11:
Preface My interest in flower-bulb
Page 12 and 13:
Acknowledgements I would like to th
Page 14 and 15:
Gordon R. Hanks Crop and Weed Scien
Page 16 and 17:
Figures 1.1 The effect of bulb stor
Page 18 and 19:
Figures/Plates xvii 7.8 Accumulatio
Page 20:
Figures/Plates of different segment
Page 23 and 24:
2 G.R. Hanks Information about the
Page 25 and 26:
4 G.R. Hanks (1999), and the polysa
Page 27 and 28:
3 2 4 1 1 3 2 4 5 Flowering in 1976
Page 29 and 30:
8 G.R. Hanks Figure 1.6 Diagrammati
Page 31 and 32:
10 G.R. Hanks (Rees, 1969). When fl
Page 33 and 34:
12 G.R. Hanks Figure 1.8 The relati
Page 35 and 36:
14 G.R. Hanks root system of commer
Page 37 and 38:
16 G.R. Hanks Cremer, M.C., Beijer,
Page 39 and 40:
18 G.R. Hanks Roh, S.M. and Lee, J.
Page 41 and 42:
20 A.C. Dweck Figure 2.1 The narcis
Page 43 and 44:
22 A.C. Dweck Julians Hertfordshire
Page 45 and 46:
24 A.C. Dweck Herefordshire, if daf
Page 47 and 48:
26 A.C. Dweck the basis of an ancie
Page 49 and 50:
28 A.C. Dweck Britten, J. and Holla
Page 51 and 52:
3 Classification of the genus Narci
Page 53 and 54:
(1) (2) (3)
Page 55 and 56:
34 B. Mathew d. Section Jonquillae
Page 57 and 58:
36 B. Mathew N. cyclamineus DC. Flo
Page 59 and 60:
38 B. Mathew 1c. Section Ganymedes
Page 61 and 62:
40 B. Mathew umbel, fragrant; peria
Page 63 and 64:
42 B. Mathew recognition whatsoever
Page 65 and 66:
44 B. Mathew Note: N. elegans shows
Page 67 and 68:
46 B. Mathew ssp. praecox Gatt. and
Page 69 and 70:
(1) (2) (3) (4)
Page 71 and 72:
50 B. Mathew Table 3.1 Horticultura
Page 73 and 74:
52 B. Mathew RHS (1958) The Classif
Page 75 and 76:
54 G.R. Hanks grown for galanthamin
Page 77 and 78:
56 G.R. Hanks such as drying stores
Page 79 and 80:
Table 4.4 Areas of Narcissus cultiv
Page 81 and 82:
60 G.R. Hanks Following planting in
Page 83 and 84:
62 G.R. Hanks lost, resulting in th
Page 85 and 86:
64 G.R. Hanks pathogen-tested nucle
Page 87 and 88:
Figure 4.1 Mean monthly weather dat
Page 89 and 90:
68 G.R. Hanks (as well as natural e
Page 91 and 92:
70 G.R. Hanks compaction and its ef
Page 93 and 94:
72 G.R. Hanks bulbs with base rot)
Page 95 and 96:
74 G.R. Hanks Figure 4.3 Modern fro
Page 97 and 98:
76 G.R. Hanks caution. Higher rates
Page 99 and 100:
78 G.R. Hanks can also be prevented
Page 101 and 102:
80 G.R. Hanks Figure 4.4 A typical
Page 103 and 104:
82 G.R. Hanks Planting date The pra
Page 105 and 106:
84 G.R. Hanks Hanks and Jones, 1986
Page 107 and 108:
86 G.R. Hanks On sloping sites, gro
Page 109 and 110:
88 G.R. Hanks Insecticide and nemat
Page 111 and 112:
90 G.R. Hanks bulb growth, especial
Page 113 and 114:
92 G.R. Hanks Figure 4.7 Changes in
Page 115 and 116:
94 G.R. Hanks methods have been tes
Page 117 and 118:
96 G.R. Hanks the boxes, exiting at
Page 119 and 120:
98 G.R. Hanks usually collected in
Page 121 and 122:
100 G.R. Hanks respond to ethylene
Page 123 and 124:
102 G.R. Hanks using thiabendazole
Page 125 and 126:
104 G.R. Hanks required for the eff
Page 127 and 128:
106 G.R. Hanks and cross-cutting, s
Page 129 and 130:
108 G.R. Hanks In practice, moulds
Page 131 and 132:
110 G.R. Hanks that, with enterpris
Page 133 and 134:
112 G.R. Hanks Balatková, V., Tupy
Page 135 and 136:
114 G.R. Hanks (Narcissus pseudonar
Page 137 and 138:
116 G.R. Hanks Flint, G.J. (1983) E
Page 139 and 140:
118 G.R. Hanks Hanks, G.R. and Rees
Page 141 and 142:
120 G.R. Hanks Khatib, K. al (1996)
Page 143 and 144:
122 G.R. Hanks Luyten, I. (1935) Ve
Page 145 and 146:
124 G.R. Hanks O’Neill, T.M., Man
Page 147 and 148:
126 G.R. Hanks Ruamrungsri, S., Rua
Page 149 and 150:
128 G.R. Hanks Thompson, P.A. (1977
Page 151 and 152:
130 G.R. Hanks Williams, M. (1996)
Page 153 and 154:
132 J.B. Briggs Table 5.1 Typical g
Page 155 and 156:
134 J.B. Briggs Table 5.3 Actual gr
Page 157 and 158:
136 J.B. Briggs Table 5.4 Actual co
Page 159 and 160:
138 J.B. Briggs Table 5.5 Capital c
Page 161 and 162:
140 J.B. Briggs ADAS (1987a) Narcis
Page 163 and 164:
142 J. Bastida and F. Viladomat Fig
Page 165 and 166:
Table 6.1 Narcissus alkaloid struct
Page 167 and 168:
Table 6.1b Continued Alkaloid name
Page 169 and 170:
Table 6.1d Tazettine type O O R1 R2
Page 171 and 172:
Table 6.1f Continued MeO Alkaloid n
Page 173 and 174:
Table 6.2 Continued Species* Alkalo
Page 175 and 176:
Page 177 and 178:
Page 179 and 180:
Page 181 and 182:
Page 183 and 184:
162 J. Bastida and F. Viladomat Tab
Page 185 and 186:
Page 187 and 188:
Page 189 and 190:
Page 191 and 192:
Page 193 and 194:
Table 6.3 Continued Alkaloid* Formu
Page 195 and 196:
Table 6.3 Continued Alkaloid* Formu
Page 197 and 198:
176 J. Bastida and F. Viladomat Tab
Page 199 and 200:
178 J. Bastida and F. Viladomat Cri
Page 201 and 202:
180 J. Bastida and F. Viladomat It
Page 203 and 204:
Page 205 and 206:
184 J. Bastida and F. Viladomat is
Page 207 and 208:
186 J. Bastida and F. Viladomat and
Page 209 and 210:
Table 6.4 Continued Alkaloid Activi
Page 211 and 212:
Page 213 and 214:
Page 215 and 216:
Page 217 and 218:
196 J. Bastida and F. Viladomat tac
Page 219 and 220:
198 J. Bastida and F. Viladomat Ang
Page 221 and 222:
200 J. Bastida and F. Viladomat Boi
Page 223 and 224:
202 J. Bastida and F. Viladomat lyc
Page 225 and 226:
204 J. Bastida and F. Viladomat Fug
Page 227 and 228:
206 J. Bastida and F. Viladomat Han
Page 229 and 230:
208 J. Bastida and F. Viladomat Kin
Page 231 and 232:
210 J. Bastida and F. Viladomat of
Page 233 and 234:
212 J. Bastida and F. Viladomat Sp
Page 235 and 236:
214 J. Bastida and F. Viladomat Wil
Page 237 and 238:
216 C. Codina and, consequently, hi
Page 239 and 240:
218 C. Codina easily lost on transf
Page 241 and 242:
220 C. Codina they might be more su
Page 243 and 244:
222 C. Codina µ g/g FW µ g/g FW 3
Page 245 and 246:
224 C. Codina Kinetin As observed i
Page 247 and 248:
226 C. Codina Table 7.3 Total produ
Page 249 and 250:
228 C. Codina Accumulation of alkal
Page 251 and 252:
230 C. Codina Accumulation of alkal
Page 253 and 254:
232 C. Codina Effect on growth and
Page 255 and 256:
234 C. Codina mg/g DW mg/g DW 0.90
Page 257 and 258:
236 C. Codina mg/g DW mg/g DW 1.4 1
Page 259 and 260:
238 C. Codina mg/g DW mg/g DW 1.5 1
Page 261 and 262:
240 C. Codina Hanks, G.R. and Jones
Page 263 and 264:
8 Narcissus and other Amaryllidacea
Page 265 and 266:
244 O.A. Cherkasov and O.N. Tolkach
Page 267 and 268:
Page 269 and 270:
Page 271 and 272:
Page 273 and 274:
Page 275 and 276:
Page 277 and 278: 9 Studies on galanthamine extractio
Page 279 and 280: 258 M. Kreh Table 9.1 Results of ga
Page 281 and 282: 260 M. Kreh relation to the qualita
Page 283 and 284: 262 M. Kreh Figure 9.3 Galanthamine
Page 285 and 286: 264 M. Kreh 2.0 flower 2 1 3 4 0 10
Page 287 and 288: 266 M. Kreh • High purity of the
Page 289 and 290: 268 M. Kreh fraction of Narcissus
Page 291 and 292: H O MeO O MeO H H HO H (1) (3) + 2
Page 293 and 294: 272 M. Kreh Gorinova, N.I., Atanass
Page 295 and 296: 274 R.M. Moraes (Katz and Taneck, 1
Page 297 and 298: 276 R.M. Moraes bulbs of many Narci
Page 299 and 300: 278 R.M. Moraes Galanthamine conten
Page 301 and 302: 280 R.M. Moraes Table 10.2 The effe
Page 303 and 304: 282 R.M. Moraes years, a yield of 1
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
Page 325 and 326: 12 Synthesis of galanthamine and re
Page 327: 306 V.N. Bulavka and O.N. Tolkachev
Page 331 and 332: 310 V.N. Bulavka and O.N. Tolkachev
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
Page 393 and 394:
Page 395 and 396:
Page 397 and 398:
Page 399 and 400:
Page 401 and 402:
16 Narcissus lectins Els J.M. Van D
Page 403 and 404:
382 E.J.M. Van Damme and W.J. Peuma
Page 405 and 406:
Page 407 and 408:
Page 409 and 410:
Page 411 and 412:
Page 413 and 414:
17 Narcissus in perfumery HISTORY C
Page 415 and 416:
394 C. Remy Figure 17.2 Flower coll
Page 417 and 418:
Figure 17.3 Narcissus flowers sprea
Page 419 and 420:
398 C. Remy CONCLUSION The use of n
Page 421 and 422:
400 C.G. Julian and P.W. Bowers Fig
Page 423 and 424:
Page 425 and 426:
Page 427 and 428:
406 C.G. Julian and P.W. Bowers sym
Page 429 and 430:
19 Review of pharmaceutical patents
Page 431 and 432:
410 J.R. Murray to certain RNA viru
Page 433 and 434:
412 J.R. Murray occurs in a two-pha
Page 435 and 436:
414 J.R. Murray cognitive function
Page 437 and 438:
416 J.R. Murray given at a time bet
Page 439 and 440:
418 J.R. Murray Hofmannor, D., Mosc
Page 441 and 442:
420 Index Backache, 403 Bacterial d
Page 443 and 444:
422 Index Divisions (classification
Page 445 and 446:
424 Index Leaf numbers, 11 Leaf sco
Page 447 and 448:
426 Index Poet’s cultivars, 34 Po
Page 449:
428 Index Subgenus (taxonomy); Ajax
show all

Narcissus and Daffodil

Create successful ePaper yourself

Delete template?

Save as template?