Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative

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Abstract

The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine. © 2013 Tabuchi et al.

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Tabuchi, T., Urabe, D., & Inoue, M. (2013). Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative. Beilstein Journal of Organic Chemistry, 9, 655–663. https://doi.org/10.3762/bjoc.9.74

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