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

被引：3

作者：

Tabuchi, Toshiki ^{[1
]}

Urabe, Daisuke ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1330033, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

关键词：

asymmetric synthesis; C-2-symmetry; catalysis; Diels-Alder reaction; Lewis acid; natural product; quaternary carbon; DIELS-ALDER REACTIONS; RING-SYSTEM; RYANODINE; TERPENOIDS;

D O I：

10.3762/bjoc.9.74

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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 C-2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

引用

页码：655 / 663

页数：9

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