Item – Theses Canada

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OCLC number
1032911097
Link(s) to full text
LAC copy
LAC copy
Author
El-Salfiti, Mohamed Kamal.
Title
Towards the Total Synthesis of Lysergic Acid via a Rhodium-catalyzed Enantioselective Desymmetrization of Substituted Oxabicycles and the Construction of Tetrasubstituted Helical Alkenes by a Palladium-catalyzed Domino Process.
Degree
MAST -- University of Toronto, 2012
Publisher
Toronto : University of Toronto, 2012.
Description
1 online resource
Notes
Includes bibliographical references.
Abstract
A synthetic approach to produce lysergic acid by virtue of an asymmetric ring opening (ARO) of symmetrical 3,6-disubstituted-7,10-hydroxymethyl bridgehead substituted oxabicycles is described. The use of a Rhodium(I)/JosiPhos(R,S) catalyst system to effect an ARO using an amine nucleophile furnishes an enantiopure tetrahydronapthalene intermediate with the amine conveniently installed at the 6 position as in lysergic acid, with appropriate stereochemistry; further which, two subsequent annulations are necessary to form the fused 3,5-substituted indole and tetrahydropyridine to complete the synthesis. Progress of this work is described herein along with future directions. The second chapter in this thesis describes the modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction under Catellani conditions. These helical alkenes possess potentially interesting photochemical properties as molecular motors / switches, and can be applicable in the materials sciences as molecular machines.
Other link(s)
hdl.handle.net
tspace.library.utoronto.ca
Subject
Rhodium.
Palladium.
Asymmetric catalysis.
Domino Reactions.
Ring-opening.
Helical Alkenes.
0490.