The use of simple hydrocarbons as starting materials for the synthesis of complex molecules relies on efficient methods for oxidation, functionalization or rearrangement. Tricarbonyl(cyclooctatetraene)iron 1  , readily prepared from COT, reacts with a variety of electrophiles to form (dienyl)iron cations 2  -4  . These steps may be regarded as branching pathways in diversity oriented synthesis. Reaction of cations 2  -4  with a variety of nucleophiles, followed by oxidative decomplexation gave the racemic polyenes 5  -7  respectively. Further manipulation of the polyenes 5  -7  can be effected by cycloaddition, oxidation, oxidative cleavage, rearrangement or reduction. Utilizing these reactions, a variety of stereochemically diverse polyhydroxy aminocycloalkanes (�aminocyclitols�) have been prepared. The inhibitory activity of these aminocyclitols against commercially available glycosidases will be reported. 

Generation of molecular complexity from simple hydrocarbons: Preparation of aminocyclitols from cyclooctatetraene

247th National Meeting (2014)

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