Thesis-Final 03 June 2011 pdf - Jacobs University

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Results and discussion Chapter 3 General synthetic procedure: The first chemical synthesis of chlorogenic acid (5-CQA) was reported by Panizzi et al. 45 years ago 306 . The natural product was prepared in seven steps from quinic acid but the overall yield was low (
Results and discussion Chapter 3 Preparation of acid chlorides of cinnamic acids: For the synthesis of cinnamic acid chlorides as mentioned by Sefkow was adopted. The cinnamic acid derivatives caffeic, ferulic and coumaric acids were reacted with Ac 2 O in pyridine in the presence of 5% 4-(dimethylamino)pyridine (DMAP, Steglich catalyst) as a nucleophilic acylation catalyst. The acetate protected compounds were obtained in good yield (91-94%) as white powder. Further reaction with oxalyl chloride, DMF in DCM, produced the acid chlorides (81-87%) as water sensitive solids in good yields. All spectroscopic datas were in full agreement with the structures. Similarly the acid chloride of 3, 4-dimethoxycinnamic acid was obtained in 93 % yield as a yellow powder. Synthesis of diacetyl caffeic acid chloride, (41) Scheme 1: Synthesis of diacetyl caffeic acid chloride (41) As it was described by Sefkow diacetyl caffeic acid chloride (41) was obtained in 92% yield by esterification of caffeic acid with two equivalents of acetic anhydride in pyridine. 5% of 4-(dimethylamino)-pyridine (DMAP, Steglich catalyst) used as catalyst in the synthesis. Synthesis of acetyl ferulic acid chloride (42), Acetyl p-coumaric acid chloride, (43), and 3, 4-dimethoxycinnamic acid chloride, (44) achieved similar way by using sufficient amount of acetic anhydride as shown in the Scheme 2, Scheme 3, Scheme 4. 53
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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)-
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: Aims and objectives As described ch
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Results and discussion Chapter 3 Fi
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Results and discussion Chapter 3 0
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Results and discussion Chapter 3 Th
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Results and discussion Chapter 3 Sc
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Results and discussion Chapter 3 di
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Results and discussion Chapter 3 Sy
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Results and discussion Chapter 3 pp
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Results and discussion Chapter 3 Sc
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Results and discussion Chapter 3 sp
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Results and discussion Chapter 3 ap
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Results and discussion Chapter 3 In
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Results and discussion Chapter 3 mu
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Results and discussion Chapter 3 Qu
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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 Sy
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Results and discussion Chapter 3 Al
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Conclusions Chapter 4 Conclusions A
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Conclusions Chapter 4 Mono-acyl chl
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Conclusions Chapter 4 The products
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Conclusions Chapter 4 Di-acyl chlor
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Conclusions Chapter 4 Poly-acyl chl
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EXPERIMENTAL Chapter 5 181
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Synthesis of starting materials Qui
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Annex Chapter 6 Acetyl ferulic acid
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Annex Chapter 6 3, 4-dimethoxycinna
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Annex Chapter 6 3, 4-O-Isopropylide
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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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