SCHEDULED MAINTENANCE
A simple approach to the bicyclo[5.3.1]undecane system present in taxanes
Abstract
A simple route for the synthesis of the bicyclo[5.3.1]undecane ring system present in taxanes has been developed. The key steps involve the cleavage of a carbon–carbon bond in the tricyclo[5.2.1.02,6]decane system 5 and a one-carbon ring enlargement of the latter to the bicyclo[5.3.1]undecane system 23. The potential generality of this ring cleavage process has been examined using various tricyclo[5.2.1.02,6]decane derivatives 5, 10 and 13 which have been prepared either through a [4 + 2] cycloaddition reaction or by annelation via alkylation of the vicinal dianion. The scope and limitations of both these routes to the synthesis of the tricyclo[5.2.1.02,6]decane derivatives have been demonstrated.
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