Online Thesis Search Results

TITLE
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
ABSTRACT
List of Patents /Publications and Conference Proceedings
CONTENTS
1. Background and Scope of the Thesis
I.1 INTRODUCTION
I.2 (2S, 3S) - AND (2S, 3R) -TETRAHYDRO-3-HYDROXY-5-OXO-2, 3-FURANDICARBOXYLIC ACIDS (1 & 2)
I.3 CHIRONS OBTAINED FROM (2S, 3S) - AND (2S, 3R) -TETRAHYDRO-3-HYDROXY-5-OXO-2, 3-FURANDICARBOXYLIC ACIDS
Chiral molecules prepared from 1 and 2 (Table 1)
2. Syntheses and Applications of Chiral γ- Hydroxy Acids or Lactones
II.1 INTRODUCTION
II.2 GARCINIA ACID
II.2.1 Biochemistry of 1Effect (-) HCA on Fatty acid synthesis and Lipogenesis
II.2.2 (-) HCA as a weight-controlling Agent
II.3 HIBISCUS ACID
II.4. ISOCITRIC ACID
II.4.1 Kreb’s cycle
II. 5 LIGNANS
II.5.1 Matairesinol
II.5.2 (-) Entero lactone
II.5.3 (-) -Arctigenin
II.5.4 (-) -Trachelogenin
II.6 AVENACIOLIDE, ISOAVENACIOLIDE AND ETHISOLIDE
II.7 XYLOBOVIDE, CANADENSOLIDE AND SPOROTHRIOLIDE
II.8 PARACONIC ACIDS
II.8.1 (-) Methylenolactocin
II.8.2 (+) Protolichersternic acid
II.8.3 (+) Nephrosteranic acid and (+) Rocellaric acid
II.8.4 (-) -Phaseolinic Acid
II.9 VERNOLEPIN AND VERNOMENIN
II.10 Frullanolide and Arbusculline
II.11 Annonaceous acetogenins
II.11.1 4-Deoxyannomontacin
II.11.2 Trilobacin
II.11.3 Squamotacin
II.12 MUCOCIN AND MUCOXIN
II.13 (-) -MURICATACIN
II.14 SECOSYRIN 1 AND 2, SYRIBUTIN1 AND 2, SYRINGOLIDE 1 AND 2
II.15 (-) -MINTLACTONE AND (+) -ISOMINTLACTONE
II.16 CINATRIN C2 AND C3
II.17 CIS AND TRANS WHISKY AND COGNAC LACTONES
II.18 FUNEBRINE, FUNEBRAL AND BISNORFUNEBRAL
II.19 (+) BLASTMYCINONE, (+) ANTIMYCINONE
II.20 APPLICATION OF CHIRAL γ-BUTYROLACTONE BASED MOLECULES INSMART MATERIALS
II.21 CONCLUSION
3. Synthesis of Analogues of the Quararibea Metabolite Chiral Enolic-g-Lactones from (2S, 3S) - and (2S, 3R) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acids
III. 1 Introduction
III.2 Quararibea Metabolite Chiral Enolic- --Lactone
III.2.1 (-) Kainic acid
III.2.2 Syntheses of Chiral Butenolides
III.3 Result and Discussion
III.3.1 Isolation of (2S, 3S) - and (2S, 3R) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acids (1 and 2)
III.3.1.1 Isolation of (2S, 3S) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acid (1)
III.3.1.2 Isolation of (2S, 3R) -Tetrahydro-3-hydroxy-5-oxo-2, 3- furandicarboxylic acid (2)
III.3.1.3 Determination of Absolute Configuration by Vibrational CircularDichroism (VCD)
III.3.1.4 Analysis of absolute configuration of (2S, 3S) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acid (1) by Vibrational Circular Dichroism (VCD)
III.3.1.5 Analysis of absolute configuration of (2S, 3R) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acid (2) by Vibrational Circular Dichroism (VCD)
III.3.2 Preparation of Dialkyl (2S, 3S) - and (2S, 3R) -tetrahydro-3- hydroxy-5-oxo-2, 3-furandicarboxylates from 1 and 2
III.3.2.1 Preparation of Dibenzyl (2S, 3S) - and (2S, 3R) -tetrahydro-3- hydroxy-5-oxo-2, 3-furandicarboxylates from 1 and 2
III.3.3 Preparation of Dialkyl 2S-2 (5H) furanone- 4, 5-dicarboxylates using Dialkyl (2S, 3S) -and (2S, 3R) - tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylates.
III.3.4 Dehydroacetylation of Dialkyl (2S, 3S) - and (2S, 3R) - Tetrahydro-3- actyloxy-5-oxo-2, 3- furandicarboxylate.
III.3.5 Phosphorous oxychloride (POCl3) in Functional Group Transformations
III.3.5.1 Vilsmeier-Haack and Bischler-Napieralski Reactions
III.3.5.2 Beckmann rearrangement
III.3.5.3 Dehydrating Agent
III.3.6 Dehydration of Dialkyl (2S, 3S) - and (2S, 3R) - tetrahydro-3- hydroxy-5-oxo-2, 3-furandicarboxylate with POCl3.
III.3.7 Dehydration of Diisopropyl (2S, 3R) - tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate with POCl3.
III.3.8 Preparation of aromatic Dialkyl-5-[ (methylsulfonyl) oxy]-2, 3-furandicarboxylates
III.3.9 Plausible mechanism for the formation of Dimethyl 2S-3-methoxy- 2 (5H) furanone-4, 5-dicarboxylate (206):
Scheme III.35: Plausible mechanism for the formation of Dimethyl-2S- 3-methoxy-2 (5H) -furanone-4, 5-dicarboxylate.
III.3.10 Plausible mechanism for the formation of Dimethy-5-[ (methylsulfonyl) oxy]-2, 3-furandicarboxylate (209)
Scheme III.36: Plausible mechanism for the formation of Dimethyl-5-[ (methylsulfonyl) oxy] -2, 3-furandicarboxylate
III.3.11 Applications of 2S- Dimethyl 4-methoxy- 5- oxo - 2, 5- dihydro- 2, 3- furandicarboxylate (206)
III.3.12 Attempted reactions of 2S-Dialkyl-4-methoxy-5-oxo-2, 5-dihydro-2, 3- furandicarboxylate
III.3.13 Chemoselective Reduction of C2 and C3 Carboxylic Group of 1
III.3.14 Efficient Site Selective Reduction Employing BH3SMe2 and Catalytic NaBH4
III.4 GENERAL EXPERIMENTAL DETAILS
III.5 EXPERIMENTAL
III.5.1 (2S, 3S) -Tetrahydro-3hydroxy-5-oxo-2, 3-furandicarboxylic acid (1)
III.5.2 (2S, 3R) -Tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylic acid (2)
III.5.3 Disodium (2S, 3S) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (5)
III.5.4 Dimethyl (2S, 3S) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (9)
III.5.5 Diethyl (2S, 3S) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (10)
III.5.6 Diisopropyl (2S, 3S) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (11)
III.5.7 Dibenzyl (2S, 3S) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (12)
III.5.8 Disodium (2S, 3R) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (6)
III.5.9 Dimethyl (2S, 3R) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (13)
III.5.10 Diethyl (2S, 3R) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (172)
III.5.11 Diisopropyl (2S, 3R) -tetrahydro-3-hydroxy-5-oxo-2, 3-furandicarboxylate (173)
III.5.12 Dibenzyl (2S, 3R) -tetrahydro-3-hydroxy-5-oxo-2, 3- furandicarboxylate (14)
III.5.13 Diisopropyl (2S, 3S) -tetrahydro-3-acetyloxy-3-acetyloxy-5-oxo-2, 3-furandicarboxylate (178)
III.5.14 Diisopropyl (2S, 3R) -tetrahydro-3-acetyloxy-5-oxo-2, 3-furandicarboxylate (180)
III.5.15 Dimethyl 3-methoxy 2 (5H) furanone 4, 5 dicarboxylate (206)
III.5.16 Diethyl 3-methoxy 2 (5H) furanone 4, 5 dicarboxylate (207)
III.5.17 Dibenzyl 3-methoxy 2- (5H) furanone 4, 5-dicarboxylate (208)
III.5.18 Diisopropyl 3-methoxy- 2- (5H) furanone 4, 5- dicarboxylate (171C)
III.5.19 Dimethyl 5-[ (methylsulfonyl) oxy] -2, 3-furandicarboxylate (209):
III.5.20 Diisopropyl 5-[ (methylsulfonyl) oxy] -2, 3-furandicarboxylate (210):
III.5.21 Isopropyl (2S, 3R) -terahydro-3-acetyloxy-3-acetyloxymethyl-5-oxo-furan-2-carboxylate (230)
4. Syntheses and Functional Application of (4S, 5S) -4- (2-Hydroxy-2, 2-diarylethyl) -2, 2-Dimethyl-α, α, α’, α’-tetraaryl-1, 3-dioxalane-4, 5-Dimethanols
IV.1 INTRODUCTION
IV.2 APPLICATIONS OF 1, 2-DIOLS
1. Chiral Synthon
2. Chiral Catalyst
IV.3 CHIRAL CATALYSIS
IV.4 Results and discussion
IV.4.1 Preparation of Trialkyl (1S, 2S) -and (1S, 2R) -1, 2-dihydroxy-1, 2, 3-propanetricarboxylates
IV.4.2 Investigation on the Absolute Configuration of Trimethyl (1S, 2S) -1, 2-dihydroxy-1, 2, 3-propane tricarboxylate
IV.4.3 Preparation of Dimethyl (4S, 5S) - and (4S, 5R) -2, 2-dialkyl-4- (2-oxo-2-methoxyethyl) -1, 3-dioxolane-4, 5-dicarboxylates
IV.4.4 Preparation of (4S, 5S) - 4 (2-hydroxy-2, 2-diphenylethyl) -2, 2-dimethyl –α, α, α’, α’- tetraaryl -1, 3-dioxalane- 4, 5-dimethanol
IV.4.5 Liquid Crystals: A Tool for study on Chirality
IV.4.5.1 Chiral Dopant
IV.4.5.2 Applications of Liquid Crystals to Studies on Chirality
IV.4.5.3 Detection of very small Optical Activities
IV.4.5.4 Determination Thermal Recemization Barrieres.
IV.4.5.6 Determination of Absolute Configurations
IV.4.6 Functional Application of (4S, 5S) -4- (2-Hydroxy-2, 2 diarylethyl) -2, 2-Dimethyl-α, α, α’, α’ -tetra aryl-1, 3-dioxalane-4, 5-dimethanols
Fig.1V.26 Polarized optical micrograph (400x) showing Finger printtexture of a cholesteric phase obtained for at10 °C.
Fig.1V.27 Polarized optical micrograph (400x) showing Focal Conictexture of a cholesteric phase obtained for at 30 °C.
IV. 7 EXPERIMENTAL
IV. 7.1 Trisodium (1S, 2S) -1, 2-dihydroxy-1, 2, 3-propanetricarboxylate (15)
IV. 7.2 Trimethyl (1S, 2S) -1, 2-dihydroxy-1, 2, 3-propanetricarboxylate (17)
IV. 7.3 Triisopropyl (1S, 2S) -1, 2 dihydroxy-1, 2, 3-propanetricarboxylate (19)
IV. 7.4 Tribenzyl (1S, 2S) -1, 2 dihydroxy-1, 2, 3-propanetricarboxylate (247) .
IV. 7.5 Trisodium (1S, 2R) -1, 2-dihydroxy-1, 2, 3-propanetricarboxylate (16):
IV. 7.6 Trimethyl (1S, 2R) -1, 2-dihydroxy-1, 2, 3-propanetricarboxylate (20):
IV. 7.7 Triisopropyl (1S, 2R) -1, 2 dihydroxy-1, 2, 3-propanetricarboxylate (22) .
IV. 7.8 Dimethyl (4S, 5S) -2, 2-dimethyl-4- (2-oxo-2-methoxyethyl) -1, 3-dioxolane-4, 5-dicarboxylate. (23)
IV. 7.9 Dimethyl (4S, 5R) -2, 2-dimethyl-4- (2-oxo-2-methoxyethyl) -1, 3-dioxolane-4, 5-dicarboxylate (25)
IV. 7.10 (4R, 5R) -2, 2-dimethyl α, α, α’, α’- tetraphenyl -1, 3-dioxalane- 4, 5-dimethanols (244) .
IV. 7.11 (4S, 5S) - 4 (2-hydroxy-2, 2-diphenyllethyl) -2, 2-dimethyl –α, α, α’, α’- tetraphenyl -1, 3-dioxalane- 4, 5-dimethanol (27)
5. Summary of the Thesis
References