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Table of Contents
Abstract .................................................................................................................................... ii
Preface ..................................................................................................................................... iv
Table of Contents ................................................................................................................... vi
List of Tables .......................................................................................................................... ix
List of Figures .......................................................................................................................... x
List of Schemes ...................................................................................................................... xx
List of Symbols and Abbreviations .................................................................................. xxiii
Acknowledgements ........................................................................................................... xxvii
Dedication ......................................................................................................................... xxviii
Chapter 1: Marine Natural Products From Benchtop to Bedside .................................... 1
1.1 Nature as a Source of Medicine ................................................................................ 1
1.2 Synthesis as an Aid to Structure Elucidation ............................................................ 6
1.3 Translating a Drug-Lead Into a Drug by Structure Activity Relationship (SAR)
Studies ……………………………………………………………………………………..10
1.4 Bioactive Marine Natural Products Reveal Novel Mechanism of Action .............. 13
1.5 Scope of Thesis ....................................................................................................... 14
Chapter 2: Synthesis and Biological Evaluation of SHIP1 Activators ........................... 16
2.1 Inhibition of PI3K Signaling by Activation of SHIP1 ............................................ 16
2.2 First Generation SHIP1 Agonist Pelorol and Analogues ........................................ 18
2.3 Synthesis of SHIP1 Activators Using a Polyene-Initiated Cationic Cascade ......... 21
2.4 Synthesis of Water Soluble Analogues to Facilitate Drug Administration ............ 25
2.5 Saturation Transfer Difference (STD) Spectroscopy NMR.................................... 38
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