Introduction 2 Fermentation and Isolation 3 Structure Determination 4 Biosynthesis 5 Metabolism 6 Chemistry 6.1 Total Synthesis 6.2 Partial Synthesis 6.3 The Interconversion of the Avermectins and Mil bemycins 6.4 Protection and Acylation 6.5 Oxidations 6.6 Alkylation 6.7 Reduction 6.8 Avermectin Aglycons and their Monosaccharide Analogues 7 Structure-Activity Relationships 8 Conclusion 9 References* Wherever avermectins are described in this Report by using only the first two identifying characters, as in A2, this refers to mixtures of the a and b analogues. In these cases, only the structure of the major component is indicated in the diagram. Where fully identified, as in B2b, this implies the use of pure compound.
Systematic modification of the presumed P1 side chain in a series of (carboxyalkyl)amino-based inhibitors of matrix metalloproteinases enabled identification of the 2-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)ethyl group as a preferred substituent imparting potent inhibition of the enzymes collagenase and gelatinase. It was subsequently found that the P2'-P3' residues in this series could be replaced by small non-peptide residues, while maintaining inhibitory potency. The imide group in this series of compounds can undergo autocatalytic hydrolysis under neutral conditions.
Photoisomerisation of 3-hydroxy-7,7-dimethylbicyclo[3.2.0]heptan-6-ones is the key step in a new route to the pheromone eldanolide while leukotriene-B4 is available through a photolytic retro[2 + 21 reaction of 2-hydroxy-7,7-dimethyl bicyclo[3.2.0]heptan-6-ones. On photolysis, substituted cyclobutanones can undergo three transformations: (a) ring expansion to give an oxacarbene, (b) decarbonylation, or (c) retro[2 + 21 cycloaddition.1 When the
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