Thesis-Final 03 June 2011 pdf - Jacobs University

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Results and discussion Chapter 3 13 C-NMR spectrum signals were consistent with the 1 H-NMR spectrum. The 13 C- NMR spectrum showed that some of the signals were overlapped due to the same kind of chemical shifts. The first peak at 21.21 ppm with three carbon intensity identified as C-38, C-39 and C-40. Then this signal followed by quinide carbons. The peak at 33.97 and 34.51 ppm identified as C-2 and C-6 due to cross peaks at 1 H 1 H-COSY and 1 H 13 C-HMQC spectrums. Another four signals of quinide carbons found at 66.15, 66.19, 76.05 and these signals were assigned to C-4, C-3 and C-5. The first carbons of quinide moiety C-1 occurred in downfield 77.12 ppm compare to other carbons of quinide with smaller signal intensity. The six sets of olefinic carbons in the region as it was expected. The first olefinic carbons occurred at 116.66, 116.88, 116.97 ppm and assigned to C-9, C-18 and C-27. These signals followed by overlapping twelve carbons of aromatic group. The signals occurred at 122.24, 122.35, 122.41, 129.45, 129.59 and 129.72 ppm assigned to C-13, C-15, C-22, C-24, C-31, C-33, C-12, C-16, C-21, C-25, C-30 and C-34. The next set of carbons occurred at 131.70, 131.71 and 131.75 ppm. This group identified as carbons of aromatic group which hasn’t got any hydrogen adjacent to it. These signals assigned to C-11, C-20, C-29 due to cross peaks at 1 H 13 C-HMQC spectrum. The second set of olefinic carbons occurred just after aromatic carbons where it was expected before. The signal at 145.13, 145.80 and 145.90 ppm assigned to C-10, C-19 and C-28 carbons due to chemical shift consideration and the cross peaks which was observed at H 1 H-COSY and 1 H 13 C- HMQC spectrum. The first set of carbonyl carbons found at 152.41, 152.62 and 152.70 ppm and this signals assigned to C-8, C-17 and C-26. Then the other three carbonyl carbons occurred at 164.91, 165.23 ppm. By looking at the signal intensity and the cross peaks at 1 H 13 C-HMQC spectrum the signal at 164.91 ppm identified as overlapping two carbonyl carbons C-14 and C-23. Then the signal at 165.23 ppm with one carbon intensity assigned to C-32. The very last part of carbonyl carbons of coumaroyl moiety was occurred at 169.14 ppm with three carbon intensity and assigned to C-35, C-36 and C-37. The carbonyl carbon of quinide moiety occurred at the end of the spectrum at 171.32 ppm and assigned to C-7. The infrared spectrum showed consistent signals at 1806, 1765, 1721 cm -1 (C=O), 1635 (C Ar =C Ar ), 1267, 1243, 1156, 1077 cm -1 (C-O) as the other spectral data. 156
Results and discussion Chapter 3 0 20 40 60 80 F1 Chemical Shift (ppm) 100 120 140 160 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0 F2 Chemical Shift (ppm) Figure 124: 1 H 13 C-HMQC spectrum of (1S, 3R, 4R, 5R)-1, 3, 4-tri-(acetyl p- coumaroyl) quinide Figure 125: IR spectrum of (1S, 3R, 4R, 5R)-1, 3, 4-tri-(acetyl p-coumaroyl) quinide 157
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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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Results and discussion Chapter 3 ch
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Page 167: 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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Page 217 and 218: 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-
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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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