Thesis-Final 03 June 2011 pdf - Jacobs University

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Results and discussion Chapter 3 2-H eq then followed by 6-H eq at 2.56 ppm and 6-H ax at 3.09 ppm. The quinide protons found at 4.85, 5.17 and 5.47 ppm. By analyzing 1 H 1 H-COSY spectrum of the product the doublet of doublet at 5.47 ppm identified H-4 due to crosspeaks to H-5 and H-3 protons. Due to chemical shift considerations the triplet at 4.85 ppm assigned to H-5 and the multiplet at 5.17 ppm assigned to H-3. 13 C-NMR showed consistent signal with 1 H-NMR spectrum. The acetyl carbons C- 11, C-12, C-13 found at 21.10, 21.16 and 21.30 ppm. 13 C-NMR spectrum along with 1 H 1 H-COSY spectrum and 1 H 13 C-HMQC spectrum allowed identification and assignments of quinide carbons. The signals at 33.76 ppm, 34.20 ppm, 65.04 ppm, 65.87 ppm, 71.68 ppm, assigned to C-2, C-6, C-3, C-4, C-5 and C-1. The following signals found at 169.30 ppm, 169.35 ppm, 171.52 ppm and 171.29 ppm. Due to chemical shift and the cross peaks at HMQC spectrum this signals assigned to C-8, C- 9, C-10 and C-7. Infrared spectrum shows strong signals for carbonayl esters at 1800, 1755 cm -1 (C=O) and the mass spectrum shows the molecular ion and fragment ions corresponding to structure of the compound. Figure 116: 13 C-NMR spectrum of 98 146
Results and discussion Chapter 3 2 3 4 5 6 F1 Chemical Shift (ppm) 7 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 F2 Chemical Shift (ppm) Figure 117: 1 H 1 H-COSY spectrum of 98 Synthesis of (1S, 3R, 4R, 5R)-1, 3, 4-tri-cinnamoyl quinide, (99)-p235 (Attempt of tetra-acyl quinic acid) Scheme 42: Synthesis of (1S, 3R, 4R, 5R)-1, 3, 4-tri-cinnamoyl quinide 147
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Synthesis of Chlorogenic Acids & Ch
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“Imagination is more important th
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Abbreviations Ac Ac 2 O AcOH MeCN C
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CONTENT Chapter 1 vi
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Content Chapter 1 Preparation of ac
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Content Chapter 1 (1S, 3R, 4R, 5R)-
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Background Chapter 2 Phenolic Phyto
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Background Chapter 2 Types of polyp
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Background Chapter 2 Stilbenes cont
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Background Chapter 2 Biosynthesis o
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Background Chapter 2 Biological act
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Background Chapter 2 terpenoids, to
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Background Chapter 2 Table 2: Bioav
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Background Chapter 2 These well kno
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Background Chapter 2 Hydroxycinnami
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Background Chapter 2 small amounts
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Background Chapter 2 Cinnamate tran
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Background Chapter 2 used in the is
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Background Chapter 2 acid is implic
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Background Chapter 2 Chlorogenic ac
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Background Chapter 2 HO O HO OH C O
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Background Chapter 2 acyl migration
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Background Chapter 2 Reported Synth
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Background Chapter 2 1-O-Cinnamoylq
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Background Chapter 2 O O O H + CinO
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Background Chapter 2 chloride gave
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Background Chapter 2 Synthesis of 1
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Background Chapter 2 Esterification
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Background Chapter 2 Synthesis of 3
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Background Chapter 2 Table 5: Chlor
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Background Chapter 2 roasting degre
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Aims and objectives As described ch
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Results and discussion Chapter 3 Pr
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Results and discussion Chapter 3 co
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Results and discussion Chapter 3 Pr
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Results and discussion Chapter 3 1.
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Results and discussion Chapter 3 Sy
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Results and discussion Chapter 3 Ta
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Results and discussion Chapter 3 Fi
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Results and discussion Chapter 3 Th
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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 Th
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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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Page 107 and 108: Results and discussion Chapter 3 1
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Page 167 and 168: Results and discussion Chapter 3 CH
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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
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Annex Chapter 6 (1S, 3R, 4R, 5R)-1-
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Annex Chapter 6 (1R,3R,4S,5R)-1-dim
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Annex Chapter 6 (1R, 3R, 4S, 5R)-1-
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Annex Chapter 6 (1R, 3R, 4S, 5R)-1-
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Annex Chapter 6 5- diacetylcaffeoyl
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Annex Chapter 6 5- acetyl p-coumaro
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Annex Chapter 6 5-cinnamoyl bisacet
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Annex Chapter 6 5-O-feruloylquinic
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Annex Chapter 6 5-O-dimethoxycinnam
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Annex Chapter 6 (1S,3R,4R,5R)-1-(β
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Annex Chapter 6 (1S,3R,4R,5R)-1-(β
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Annex Chapter 6 (1S,3R,4R,5R) 1- (
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Annex Chapter 6 (1S,3R,4R,5R)-3, 4-
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Annex Chapter 6 (1S,3R,4R,5R)-3,4-b
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Annex Chapter 6 (1S,3R,4R,5R)-1,3-d
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Annex Chapter 6 (1S,3R,4R,5R)-1,3-b
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Annex Chapter 6 (1S,3R,4R,5R)-1,4-d
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Annex Chapter 6 Quinide tri-acetate
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Annex Chapter 6 (1S, 3R, 4R, 5R)-1,
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Annex Chapter 6 745 [M+H], 544 [M-C
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Annex Chapter 6 (C-24), 121.95 (C-3
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Annex Chapter 6 (acetylferuloyl) qu
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REFERENCES Chapter 6 253
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References Chapter 6 21 D. Strack,
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References Chapter 6 62 K. Herrmann
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References Chapter 6 104 N. Shibuya
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References Chapter 6 148 B. Möller
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References Chapter 6 187 M. Nardini
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References Chapter 6 221 M. F. Andr
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References Chapter 6 264 L. Panizzi
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References Chapter 6 303 J. Hucke,
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