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

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 C2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

Keywords

• asymmetric synthesis
• C2-symmetry
• catalysis
• Diels–Alder reaction
• Lewis acid
• natural product
• quaternary carbon