SYNTHESIS OF POLYCYCLIC CYCLOBUTANE DERIVATIVES BY TANDEM INTRAMOLECULAR MICHAEL-ALDOL REACTION UNDER 2 COMPLEMENTARY CONDITIONS - TBDMSOTF-ET3N AND TMSI-(TMS)2NH

被引:52
作者
IHARA, M
TANIGUCHI, T
MAKITA, K
TAKANO, M
OHNISHI, M
TANIGUCHI, N
FUKUMOTO, K
KABUTO, C
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN
[2] TOHOKU UNIV,FAC SCI,INSTRUMENTAL ANAL CTR CHEM,SENDAI,MIYAGI 980,JAPAN
关键词
D O I
10.1021/ja00071a024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The treatment of alpha,beta-unsaturated esters having a ketone function at an appropriate position with either TBDMSOTf in the presence of Et3N or TMSI in the presence of (TMS)2NH provided, via a tandem intramolecular Michael-aldol reaction sequence, several different types of cyclobutane derivatives. The two reaction conditions were complementary. Tricyclo[4.2.1.0(3,8)]nonanes 34 and 55, tricyclo[5.1.1.0(4,8)]nonane 40,tricyclo[5.4.0.0(3,7)]undecane 51, tetracyclo[5.4.0.0(3,7).0(9,11)]undecane 45, and the bicyclo[3.2.0]heptanes 56, 57, and 58, which have structures either partially or completely similar to those of endiandric acids A (1a), B (1b), and C (2), trihydroxydecipiadiene (3), lintenone (4), italicene (5), and filifolone (6), were stereoselectively synthesized by the tandem reaction.
引用
收藏
页码:8107 / 8115
页数:9
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