Thesis-Final 03 June 2011 pdf - Jacobs University

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Abbreviations for NMR NMR COSY HMQC HMBC NOESY bs s d dd ddd t m q J Hz Nuclear magnetic resonance 1 H- 1 H Correlation spectroscopy Heteronuclear Multiple Quantum Coherence (heteronuclear correlation spectroscopy) Heteronuclear Multiple Bond correlation Nuclear Overhauser Effect Spectroscopy broad signal singlet doublet doublet of doublet doublet of doublet of doublet triplet multiplet quartet coupling constant hertz Abbreviations for MS MS Mass Spectrometry CI chemical ionization EI electron ionization m/z mass-to-charge ratio M+ parent molecular ion HPLC High Performance Liquid Chromatography LC-MS Liquid Chromatography Mass Spectroscopy v
CONTENT Chapter 1 vi
Page 1 and 2: Synthesis of Chlorogenic Acids & Ch
Page 3 and 4: “Imagination is more important th
Page 5: Abbreviations Ac Ac 2 O AcOH MeCN C
Page 9 and 10: Content Chapter 1 Preparation of ac
Page 11 and 12: Content Chapter 1 (1S, 3R, 4R, 5R)-
Page 13 and 14: Background Chapter 2 Phenolic Phyto
Page 15 and 16: Background Chapter 2 Types of polyp
Page 17 and 18: Background Chapter 2 Stilbenes cont
Page 19 and 20: Background Chapter 2 Biosynthesis o
Page 21 and 22: Background Chapter 2 Biological act
Page 23 and 24: Background Chapter 2 terpenoids, to
Page 25 and 26: Background Chapter 2 Table 2: Bioav
Page 27 and 28: Background Chapter 2 These well kno
Page 29 and 30: Background Chapter 2 Hydroxycinnami
Page 31 and 32: Background Chapter 2 small amounts
Page 33 and 34: Background Chapter 2 Cinnamate tran
Page 35 and 36: Background Chapter 2 used in the is
Page 37 and 38: Background Chapter 2 acid is implic
Page 39 and 40: Background Chapter 2 Chlorogenic ac
Page 41 and 42: Background Chapter 2 HO O HO OH C O
Page 43 and 44: Background Chapter 2 acyl migration
Page 45 and 46: Background Chapter 2 Reported Synth
Page 47 and 48: Background Chapter 2 1-O-Cinnamoylq
Page 49 and 50: Background Chapter 2 O O O H + CinO
Page 51 and 52: Background Chapter 2 chloride gave
Page 53 and 54: Background Chapter 2 Synthesis of 1
Page 55 and 56: Background Chapter 2 Esterification
Page 57 and 58:
Background Chapter 2 Synthesis of 3
Page 59 and 60:
Background Chapter 2 Table 5: Chlor
Page 61 and 62:
Background Chapter 2 roasting degre
Page 63 and 64:
Aims and objectives As described ch
Page 65 and 66:
Results and discussion Chapter 3 Pr
Page 67 and 68:
Results and discussion Chapter 3 co
Page 69 and 70:
Results and discussion Chapter 3 Pr
Page 71 and 72:
Results and discussion Chapter 3 1.
Page 73 and 74:
Results and discussion Chapter 3 Sy
Page 75 and 76:
Results and discussion Chapter 3 Ta
Page 77 and 78:
Results and discussion Chapter 3 Fi
Page 79 and 80:
Page 81 and 82:
Page 83 and 84:
Page 85 and 86:
Results and discussion Chapter 3 Th
Page 87 and 88:
Results and discussion Chapter 3 an
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Results and discussion Chapter 3 20
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Results and discussion Chapter 3 Ta
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Results and discussion Chapter 3 Ge
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Results and discussion Chapter 3 pp
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Results and discussion Chapter 3 ch
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Results and discussion Chapter 3 Sc
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Results and discussion Chapter 3 di
Page 129 and 130:
Results and discussion Chapter 3 gr
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Page 135 and 136:
Results and discussion Chapter 3 pp
Page 137 and 138:
Results and discussion Chapter 3 Sc
Page 139 and 140:
Results and discussion Chapter 3 sp
Page 141 and 142:
Results and discussion Chapter 3 ap
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Page 145 and 146:
Results and discussion Chapter 3 In
Page 147 and 148:
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Results and discussion Chapter 3 mu
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Page 155 and 156:
Page 157 and 158:
Results and discussion Chapter 3 Qu
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Page 163 and 164:
Results and discussion Chapter 3 In
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Results and discussion Chapter 3 CH
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Results and discussion Chapter 3 Al
Page 183 and 184:
Conclusions Chapter 4 Conclusions A
Page 185 and 186:
Conclusions Chapter 4 Mono-acyl chl
Page 187 and 188:
Conclusions Chapter 4 The products
Page 189 and 190:
Conclusions Chapter 4 Di-acyl chlor
Page 191 and 192:
Conclusions Chapter 4 Poly-acyl chl
Page 193 and 194:
EXPERIMENTAL Chapter 5 181
Page 195 and 196:
Synthesis of starting materials Qui
Page 197 and 198:
Annex Chapter 6 Acetyl ferulic acid
Page 199 and 200:
Annex Chapter 6 3, 4-dimethoxycinna
Page 201 and 202:
Annex Chapter 6 3, 4-O-Isopropylide
Page 203 and 204:
Annex Chapter 6 1-(β, β, β-trich
Page 205 and 206:
Annex Chapter 6 (1S, 3R, 4R, 5R)-1-
Page 207 and 208:
Page 209 and 210:
Page 211 and 212:
Annex Chapter 6 (1R,3R,4S,5R)-1-dim
Page 213 and 214:
Annex Chapter 6 (1R, 3R, 4S, 5R)-1-
Page 215 and 216:
Annex Chapter 6 (1R, 3R, 4S, 5R)-1-
Page 217 and 218:
Annex Chapter 6 5- diacetylcaffeoyl
Page 219 and 220:
Annex Chapter 6 5- acetyl p-coumaro
Page 221 and 222:
Annex Chapter 6 5-cinnamoyl bisacet
Page 223 and 224:
Annex Chapter 6 5-O-feruloylquinic
Page 225 and 226:
Annex Chapter 6 5-O-dimethoxycinnam
Page 227 and 228:
Page 229 and 230:
Annex Chapter 6 (1S,3R,4R,5R)-1-(β
Page 231 and 232:
Annex Chapter 6 (1S,3R,4R,5R)-1-(β
Page 233 and 234:
Page 235 and 236:
Page 237 and 238:
Page 239 and 240:
Annex Chapter 6 (1S,3R,4R,5R) 1- (
Page 241 and 242:
Annex Chapter 6 (1S,3R,4R,5R)-3, 4-
Page 243 and 244:
Annex Chapter 6 (1S,3R,4R,5R)-3,4-b
Page 245 and 246:
Annex Chapter 6 (1S,3R,4R,5R)-1,3-d
Page 247 and 248:
Annex Chapter 6 (1S,3R,4R,5R)-1,3-b
Page 249 and 250:
Annex Chapter 6 (1S,3R,4R,5R)-1,4-d
Page 251 and 252:
Annex Chapter 6 Quinide tri-acetate
Page 253 and 254:
Annex Chapter 6 (1S, 3R, 4R, 5R)-1,
Page 255 and 256:
Page 257 and 258:
Page 259 and 260:
Annex Chapter 6 745 [M+H], 544 [M-C
Page 261 and 262:
Annex Chapter 6 (C-24), 121.95 (C-3
Page 263 and 264:
Annex Chapter 6 (acetylferuloyl) qu
Page 265 and 266:
REFERENCES Chapter 6 253
Page 267 and 268:
References Chapter 6 21 D. Strack,
Page 269 and 270:
References Chapter 6 62 K. Herrmann
Page 271 and 272:
References Chapter 6 104 N. Shibuya
Page 273 and 274:
References Chapter 6 148 B. Möller
Page 275 and 276:
References Chapter 6 187 M. Nardini
Page 277 and 278:
References Chapter 6 221 M. F. Andr
Page 279 and 280:
References Chapter 6 264 L. Panizzi
Page 281:
References Chapter 6 303 J. Hucke,
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