Total Synthesis of Natural Products:
Design Strategies and Concepts
Liam Cox
CHM4M2
Course Contents
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I
Issues of Selectivity in Oxidation
I.A Oxidation of alcohols
I.B Epoxidation
I.C Olefin Dihydroxylation and Related Reactions
I.D Allylic Oxidation
II
Issues of Selectivity
in Reduction
II.A Reduction of Carboxylic Acid Derivatives and Related Functionality
II.B Stereoselective Reduction of Prochiral Ketones
II.C Other Methods of Reduction
II.D Hydrogenation with Hydrogen and a Transition Metal Catalyst
II.E Dissolving Metal Reductions
II.F Free Radical Reductions
III
Enolate Chemistry
III.A Revision
III.B Regioselective Enolate Formation
III.C Stereoselective Enolate Formation - Control of E / Z
Enolate Geometry
III.D Reactions of Enolates
III.E The Crossed Aldol Reaction
IV
Logical and
Strategic Bond Disconnections
IV.A How do we Assess the Quality of a Synthesis
IV.B Analysing a Molecule with a View to
Synthesis
IV.C Acyl Anion Equivalents
V
Lycopodine
V.A Heathcock Synthesis
V.B Stork Synthesis
VI
Protecting Groups and
Orthogonal Protection Strategies
VI.A Desired Properties of Protecting Groups
VI.B Chemical Synthesis of a Trisaccharide
VII
Tandem Reactions
VII.A Johnson's Synthesis of Progesterone
VII.B Curran's Synthesis of Hirsutene
VIII
Fortuitous Symmetry
Elements
VIII.A Two-Directional Synthesis
IX
Biological Methods of
Control
IX.A Enzymes in Synthesis
IX.B Hydrolytic Enzymes - Lipases, Esterases,
Proteases and Amidases
IX.C Anything Nature can do we can do better? A
Biomimetic Enzyme - Catalytic Enantioselective Acylation
IX.D Enzymatic Oxidation
IX.E Reduction Reactions
X Erythronolides and Related Molecules - Case Studies
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