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Thesis Details
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TITLE
DEDICATION
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
CONTENTS
List of Patents / Publications and Conference Proceedings
ABSTRACT
I. Background and Scope of the Thesis
I.1 Introduction
Chiral molecule prepared from Garcinia acid or Hibiscus acid
II. Synthesis of Enantiomerically Pure Pyrrolidines
II.1 Introduction
II.2 General Strategies for the synthesis of chiral pyrrolidines
II.2.i Synthesis employing hydroxy acids
Table II.2Enantiomerically pure molecules obtained from Tartaric acid
II 2.ii Radical cyclization of bis-homoallylic amines
II.2.iii Electrophilic cyclization
II.2.iv Aminomercuration
II.2.v Intermolecular cyclization of chiral allylsilanes with imines
II.2.vi 1, 3-Dipolarcycloadditions
II.2.vii Ring contraction
II.2.viii Reductive amination of azidoketones
II 2.ix Cyclizations by SN2 nucleophilic substitution
II.2.x Trans amination of 1-4 dihydroxy derivative
II.2.xi Bicyclic amino derivatives as chiron
II.2.xii Carbohydrate chirons
II.2.xiii L-serine derived chiral synthon
ll.2.xiv Miscellaneous synthesis of pyrrolidines
III. Synthesis of Chiral Pyrrolidinediones and Related Molecules Using (+) and (-) 2-Hydroxycitric Acid Lactones
III.1 Introduction
III.2 Results and Discussions
III.2.i isolation of (2S, 3S-Tetrahydro-3-hydroxy-5-oxo-2, 3 furandicarboxylic acid
III.2.ii Isolation of (2S, 3R-Tetrehydro-3-hydroxy-5-oxo-2, 3 furandicarboxylic acid
III.2.iii Syntheses of pyrrolidirediones from Garcinia acid
III.2.iv (3aS, 6aS) -5[2- (3, 4-dimethoxy phenyl) ethyl]-3a-hydroxy dihydro-2H-furo[2, 3-c]pyrrole-2, 4, 6[3H, 5H]-trione
III.2.v Mescaline isocitrimide lactone
III 2.vi Reactions of Hibiscus acid with alkyl amines
III.2.vii Reactions of trimethyl esters of Garcinia and Hibiscus acids with alkyl amines
III.2.viii Future Prospects as supramolecular species
III.3 General Experimental Details
III.4 Experimental
IV. Reactions of Pyrrolidinediones
IV. 1 Introduction
IV.2 Results and Discussion
IV.2.i Attempted reduction of (3aS, 6aS) -3a- (acetyloxy) dihydro-5- (phenylmethyl) --6H-furo[ 2, 3-c] pyrrole-2, 4, 6 (311, 4H) -trione with NaBH4
IV.2.ii Attempted reduction of (3aS, 6aS) -3a- (acetyloxy) dihydro-5 (phenylmethyl) -6H-furo[ 2, 3-c] pyrrole-2, 4, 6 (3H, 4H) -trione with BH3
lV.2.iii Reduction of (3aS, 6aS) -3a- (acetyloxy) dihydro-5 (phenylmethyl -6H-furo[ 2, 3-c] pyrrole-2, 4, 6 (3H, 4H) -trione with LiAIH4
IV.3 Experimental
V. Stereo structural Evaluation of (2S, 3S) and (2S, 3R) tetrahydro-3-hydroxy-5 oxo-2, 3-furandicarboxylicacids and related Pyrrolidinediones.
V.1 Introduction
V.2 Existing methods and their disadvantages
V.3 Vibrational Circular Dichroism
V.4. Investigation on the absolute configuration of Garcinia acid
V.5 Investigations on the absolute configuration of Hibiscus acid
V.6. VCD Analysis of (3aS, 6aS) -3a- (acetyloxy) dihydro-5- (phenyl methyl) 6H-furo[2, 3-c] pyrrole-2, 4, 6 (3H, 4H) -trione
V.7 Stereo chemical investigations of 225b, Assignment of AC
V.8 Experiment
V.9 Computations
VI. Summary of the Thesis
References