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Updated: May 12, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
Toshiki Tabuchi1, Daisuke Urabe, Masayuki Inoue
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 133-0033 Japan.
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.
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