AN IMPROVED SYNTHESIS OF (+/-)-OTONECINE AND A SYNTHESIS OF A 12-MEMBERED OTONECINE DIESTER

被引:10
作者
NIWA, H
SAKATA, T
YAMADA, K
机构
[1] Department of Chemistry, Faculty of Science, Nagoya University, Chikusa
关键词
D O I
10.1246/bcsj.67.2345
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(+/-)-4-Methyl-1-phenylthio-8-oxa-4-azabicyclo[5.2.1]decane-9,10-dione was efficiently converted into (+/-)-otonecine, which was regioselectively coupled with (E)-2-ethylidenehexanedioic acid to give a 12-membered otonecine diester.
引用
收藏
页码:2345 / 2347
页数:3
相关论文
共 6 条
[1]   PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].
BODEN, EP ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395
[2]  
MATTOCKS AR, 1986, CHEM TOXICOLOGY PYRR, pCH1
[3]   TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID POSSESSING AN 11-MEMBERED RETRONECINE DILACTONE [J].
NIWA, H ;
OGAWA, T ;
OKAMOTO, O ;
YAMADA, K .
TETRAHEDRON, 1992, 48 (48) :10531-10548
[4]  
NIWA H, 1983, TETRAHEDRON LETT, V51, P5731
[5]   PYRROLIZIDINE ALKALOIDS [J].
ROBINS, DJ .
NATURAL PRODUCT REPORTS, 1993, 10 (05) :487-496
[6]   TIN(IV)-CATALYZED LACTONIZATION OF OMEGA-HYDROXY TRIFLUOROETHYL ESTERS [J].
WHITE, JD ;
GREEN, NJ ;
FLEMING, FF .
TETRAHEDRON LETTERS, 1993, 34 (22) :3515-3518