Dicobaltoctacarbonyl species in organic synthesis : a novel route into tricyclic fused ring systems (original) (raw)

2009

Abstract

This thesis describes the modern uses of cobalt carbonyl complexes in organic synthesis, by focusing primarily on the Pauson-Khand Reaction (PKR). This is where an alkyne, alkene and a dicobalt complex react in a (2+2+1) cycloaddition producing an cyclopentenone adduct. The cyclopentadienone products of the PKR were used in the synthesis of hetero fused tricyclic ring systems using a diastereoselective and regioselective chemical synthesis via the addition of soft organometallic nucleophiles: The nucleophilic addition of such species allowed a spontaneous cyclocondensation that gave fused ring systems with known biological activity prevalent in a wide range of natural products. This unique synthesis was then applied to non-hetero fused tricyclic ring systems affording a triquinane skeleton analogue which possess significant levels of biological activity. These syntheses were achieved by way of a three-step sequence after an initial PKR. A 1,4-Michael addition was followed by a 1,5-c...

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