Solution and Solid Phase Synthesis of Unusual a-Amino Acids From

23 Summary ................................................................................................................... 72
2.4 Experimental . 73
2.5 References ........................ ,. ..................................................................................... 97
Chapter Three
Synthesis d Vinylglycine
Introduction .............................................................................................................
3.1.1 Isolation and Biological Activity ...................................................................
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.........................................
3.1.2 Synthesis of Racemic Vinylglycines . .
3.1.3 Synthesis of Optically Active Vinylglycine .......................................................
3.1.4 Synthesis of Labelled fi y U a a e d n o Acrds .......................................
Resuïts and Discussion: Synthesis of Vinylglyciw from Serine ..........................
3.2.1 Tuhi Reaction of Cbz-L-Ser(ald)OBO ester 3.37
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3.2.2 Peterson Olefination of Cbz- L-Ser(ald)OBO ester 3.3 7 ..................................
3.2.3 Removal of Protecting Groups ..................................................................... 119
3.3 Summary ............................................................................................................. 121
3.4 Experïmental ............................................................................................................ 122
3.5 References ............................................................................................................. 131
Chapter Four
Stereosclective Synthesis of @ubstituted Glutsmic Acids
4.1 Introduction ............................................................................................................ 136
4.1.1 Isola fion ........................................................................................................... 136
4.1.2 Biological Activity ............................................................................................ 138
4.1.3 Synthesis of Racemic pSubstituted Glutamic Acids ......................................... 141
4.1.3. 1 Synthesis of ysubstituted Glutamic Acids: General Racemic
Methods ............................................................................................... 141
4.1.4 Synthesis of Optically Active ysubstituted Glufamic Acids ............................ 143
4.1.4.1 Glycine Enolates ..................................................................................... 143