Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
Toshiki Tabuchi, Daisuke Urabe, Masayuki Inoue
Beilstein Journal of Organic Chemistry · 2013
doi:10.3762/bjoc.9.74 (opens in a new tab)
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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 C2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.
Abstract licence: CC BY
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