ࡱ> UWT` Cbjbj >444&4&4&h&,&\B0'0':j'j'j'I(I(I(BBBBBBB$qChE*BP+E(I(P+P+*Bj'j'?B^0^0^0P+j'j'B^0P+B^0^0P?|@j'$' @7O4&-?BUB0B?mF.6mF$@mF@<I()^0)l)YI(I(I(*B*B/dI(I(I(BP+P+P+P+d!4&4& UNIVERSITY OF CALIFORNIA, IRVINE Title DISSERTATION Submitted in partial satisfaction of the requirements for the degree of DOCTOR OF PHILOSOPHY in Chemistry by Your Name Dissertation Committee: Professor Scott D. Rychnovsky, Chair Professor Name Professor Name Year Year Your Name The dissertation of Your Name is approved and is acceptable in quality and form for publication on microfilm _________________________ _________________________ _________________________ Committee Chair University of California, Irvine Year Dedication TABLE OF CONTENTS LIST OF FIGURES vi LIST OF SCHEMES vii LIST OF TABLES viii LIST OF ABBREVIATIONS x ACKNOWLEDGEMENTS xi CURRICULUM VITAE xiii ABSTRACT OF DISSERTATION xvi Chapter 1: LIST OF FIGURES LIST OF SCHEMES LIST OF TABLES LIST OF ABREVIATIONS Angstroms Ac Acetyl Atm Atmosphere BF3(OEt2 Borontrifluoride diethyl etherate BINOL 2,2(-Bis(diphenylphosphino)-1,1(-binapthol Bn Benzyl Bp Boiling point Bu Butyl CI Chemical ionization CSA Camphorsulfonic acid d day(s) DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DIBAL-H Diisobutylaluminum hydride DMAP 4-Dimethylaminopyridine DMF N,N-Dimethylformamide dr Diastereomeric ratio DTBMP 2,6-Di-tert-butyl-4-methylpyridine ee Enantiomeric excess EI Electron Impact equiv Equivalents ESI Electrospray ionization GC Gas chromatography h hour(s) HMDS 1,1,1,3,3,3-Hexamethyldisilazane HRMS High resolution mass spectrometry Hz Hertz i iso IR Infrared spectrometry j Coupling constant LAH Lithium aluminium hydride LiDBB Lithium di-tert-butylbiphenolide LDA Lithium diisopropylamide micro m milli M Molar mCPBA 3-Chloroperoxybenzoic acid min minute(s) Me Methyl MPLC Medium pressure liquid chromatography MHz Megahertz NMR Nuclear magnetic resonance Ph Phenyl ppm parts per million RT Room temperature t tert TBAF Tetrabutylammonium fluoride TBDPS tert-butyldiphenylsilyl TBS tert-butyldimethylsilyl TEMPO 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical THF Tetrahydrofuran THP Tetrahydropyran TIPS Triisopropylsilyl TLC Thin layer chromatography TMS Trimethylsilyl TSOH 4-Toluenesulfonic acid ACKNOWLEDGEMENTS CURRICULUM VITAE Your Name ABSTRACT OF DISSERTATION Title by Your Name Doctor of Philosophy in Chemistry University of California, Irvine, Year Professor Scott D. 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