Enantioselective synthesis of trans-fused bicyclo[5.3.0]decane systems via a tandem [4+3] cycloaddition-Nicholas reaction

Article abstract of DOI:10.1016/S0040-4039(99)01336-2

An enantioselective synthetic methodology to prepare trans-fused bicyclo[5.3.0]decane systems is presented. It is a very versatile methodology based on two key reactions: [4+3] cycloaddition reaction (to generate the seven-membered ring) and the Nicholas reaction (that facilitates the insertion of the five-membered ring). This methodology allows the easy preparation of a wide range of bioactive natural products containing the transfused bicyclo[5.3.0]decane system. The application of this methodology to the enantioselective synthetic approach to the pseudoguaiane carbon- skeleton is described.