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

Beilstein Journal of Organic Chemistry

Masayuki Inoue¹  Toshiki Tabuchi¹  Daisuke Urabe¹ 

[1] Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 133-0033 Japan;

关键词: asymmetric synthesis;    C2-symmetry;    catalysis;    Diels–Alder reaction;    Lewis acid;    natural product;    quaternary carbon;   

DOI  :  10.3762/bjoc.9.74

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown