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Asymmetric Synthesis of Carbocycles by Intramolecular Conjugate Displacement & Synthetic Studies on Sorbicillactone A Open Access


Other title
asymmetric synthesis of carbocycles
optically pure carbocycles
intramolecular conjugate displacement
sorbicillactone A
Type of item
Degree grantor
University of Alberta
Author or creator
Sreedharan, Dinesh
Supervisor and department
Derrick, L. J. Clive (chemistry)
Examining committee member and department
Curtis, J (Agricultural, Life & Environmental Sciences)
Liang, Li (Chemistry)
West, F. G (Chemistry)
Vederas, John (Chemistry)
Chong, M. J (Chemistry, University of Waterloo))
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
The first chapter of this thesis describes an intramolecular conjugate displacement (ICD) for the asymmetric synthesis of carbocycles using a carbon nucleophile. The precursors for ICD were synthesized by Morita-Baylis-Hillman reaction between (5R)-5-(l-menthyloxy)-2(5H)-furanone and aldehydes, which carry a geminal phenylthio groups in the γ or δ position. Acetylation of the resulting hydroxyl group, followed by oxidation of the phenylthio groups to phenylsulfonyl groups gave the desired ICD precursor which, on treatment with a base, underwent ring closure by intramolecular conjugate displacement. Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle. The second chapter describes studies aimed at the synthesis of the bioactive marine alkaloid sorbicillactone A. During this project, much of the carbon skeleton of sorbicillactone A was assembled, and studies to finish the total synthesis are in progress. The key reactions involved in this project are radical-mediated cyclization to synthesize the bicyclic core, 1,4 addition of a phenyldimethylsilyl unit, followed by trapping of the intermediate with methyl iodide and, finally, a one pot process for ketal protection and iodolactonization. After the successful installation of nitrogen at C-3, current research is directed at the installation of a methyl group at the same C-3 position.
This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for the purpose of private, scholarly or scientific research. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
Citation for previous publication
Sreedharan, D. T.; Clive, D. L. J. Org. Biomol. Chem. 2013, 11, 3128-3144.

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File title: 01 Dinesh's complete Thesis with corrections for FGSR (without examiner names) 2013 November 18
File author: Derrick Clive
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