This thesis describes two main programmes: the synthesis of a new class of homochiral amines and the synthesis of ketone analogues of 3a-esterified tropane alkaloids. In chapter one, a scaled-up synthesis of (5)-a-(diphenylmethyl)pyrrolidine 1 is described. The key hydrogenation step of the oxazolidinone intermediate 2 was extended to the synthesis of the other chiral amines 70, 73, 76, 79 and 82. Hydrogenation of the oxazolidinones proceeded in good yields (71 - 87 %) and was not susceptible to racemisation. Thus, a convenient route from amino acid ester hydrochlorides (S)-valine 65, (S)-phenylalanine 66, (S)-alanine 67, (S)-isoleucine 68 and (S)-leucine 69 allowed a range of novel chiral amines to be prepared. In chapters two and three, a...
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.Vita.Includes bibli...
The following dissertation presents a series of chiral pool approaches to amine-containing natural p...
This thesis describes the attempted syntheses of polyamine based peptide toxins (enzymatically) and ...
Tropane alkaloids are a long-known class of compounds possessing an 8-azabicyclo[ 3.2.1]octane skele...
A synthesis of the ketone analogues of three naturally occurring tropane esters has been developed a...
Diels-Alder cycloaddition between 1,3-cycloheptadiene (or its derivatives) and benzyl nitrosoformate...
This Thesis covers three areas of research relating to Pyrrolizidine Alkaloids: (a) Synthesis of PA ...
This thesis is split into three sections based on three different areas of research. In the first se...
Tropane alkaloids, containing the 8-azabicyclo[3.2.1]octane ring system, are widespread in Nature. T...
Tropane alkaloids are an important class of biologically active small molecules characterized by the...
The biosynthesis of tropane and tobacco alkaloids has been extensively studied since the 1950's. The...
Includes bibliographical references.This project was initiated by the observation that a natural gly...
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the t...
Chapter One describes several natural products derived from the amino acid tryptophan including the ...
1,4-Functionalisation of cyclohepta-l,3-diene using a nitroso-cycloaddition strategy provided precur...
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.Vita.Includes bibli...
The following dissertation presents a series of chiral pool approaches to amine-containing natural p...
This thesis describes the attempted syntheses of polyamine based peptide toxins (enzymatically) and ...
Tropane alkaloids are a long-known class of compounds possessing an 8-azabicyclo[ 3.2.1]octane skele...
A synthesis of the ketone analogues of three naturally occurring tropane esters has been developed a...
Diels-Alder cycloaddition between 1,3-cycloheptadiene (or its derivatives) and benzyl nitrosoformate...
This Thesis covers three areas of research relating to Pyrrolizidine Alkaloids: (a) Synthesis of PA ...
This thesis is split into three sections based on three different areas of research. In the first se...
Tropane alkaloids, containing the 8-azabicyclo[3.2.1]octane ring system, are widespread in Nature. T...
Tropane alkaloids are an important class of biologically active small molecules characterized by the...
The biosynthesis of tropane and tobacco alkaloids has been extensively studied since the 1950's. The...
Includes bibliographical references.This project was initiated by the observation that a natural gly...
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the t...
Chapter One describes several natural products derived from the amino acid tryptophan including the ...
1,4-Functionalisation of cyclohepta-l,3-diene using a nitroso-cycloaddition strategy provided precur...
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.Vita.Includes bibli...
The following dissertation presents a series of chiral pool approaches to amine-containing natural p...
This thesis describes the attempted syntheses of polyamine based peptide toxins (enzymatically) and ...