Rhodium(I)-Catalyzed [(3+2+2)] Carbocyclization Reactions of ACPs in Total Synthesis: Towards the Preparation of Tremulane Sesquiterpene Natural Products
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Authors
Dushnicky, Molly
Date
2015-09-01
Type
thesis
Language
eng
Keyword
Rhodium , Organic Chemistry , Carbocyclization , Natural Products , Chemistry , Total Synthesis
Alternative Title
Abstract
This thesis is divided into two main chapters. Chapter 1 focuses on transition metal-catalyzed higher-order carbocyclization reaction whilst Chapter 2 focuses on the total synthesis of tremulane sesquiterpene natural products.
Chapter one of this thesis describes the optimization and development of the diastereoselective rhodium-catalyzed intramolecular [(3+2+2)] carbocyclization reaction of dieneyne alkylidenecyclopropanes. The chapter commences with an introduction to transition metal-catalyzed higher-order carbocyclization reactions, with a strong focus on [3+2+2] carbocyclization reactions. Section 1.2 describes our development of the diastereoselective rhodium-catalyzed intramolecular [(3+2+2)] carbocyclization reaction. This section highlights the optimal reaction conditions, scope, and generality of our methodology.
Chapter two of this thesis focuses on the total synthesis of three tremulane sesquiterpene natural products. This section begins with an introduction to the tremulane family of natural products, followed by a summary of previous syntheses of two natural products. Section 2.1.4 highlights the challenges faced in the preparation of the core of the outlined target compounds. Following, section 2.1.5 outlines the successful generation of epi-(±)-tremulenolide A, epi-(±)-tremuelenediol A, and epi-(±)-ceriponol D.
Description
Thesis (Master, Chemistry) -- Queen's University, 2015-08-28 11:22:56.201
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This publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.
This publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.
ProQuest PhD and Master's Theses International Dissemination Agreement
Intellectual Property Guidelines at Queen's University
Copying and Preserving Your Thesis
Creative Commons - Attribution - CC BY
This publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.
This publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.