Substrate dependent intramolecular Pauson-Khand reaction of carbohydrate exo-methylene derivatives. Unexpected formation of fused ''[4.1.0] bicycloheptene-pyranose'' tricyclic product

被引:30
作者
Borodkin, VS
Shpiro, NA
Azov, VA
Kochetkov, NK
机构
[1] ND Zelinsky Inst. of Organ. Chemitry, Russian Academy of Sciences, 117913 Moscow
关键词
D O I
10.1016/0040-4039(96)00046-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Attempted Pauson-Khand cyclisation of exo- methylene carbohydrate enynic substrates is described. 3-Exo methylene derivative cyclises to give a normal Pauson-Khand product while cyclisation of a 4-exo methylene analog follows a previously unreported pathway to give fused ''[4.1.0] bicycloheptene pyranose'' tricyclic product.
引用
收藏
页码:1489 / 1492
页数:4
相关论文
共 22 条
[21]   DISPLACEMENT OF SUGAR TRIFLATES WITH C-NUCLEOPHILES - D-GLUCOPYRANOSE AND D-RIBOFURANOSE CHAIN EXTENSION AND FUNCTIONALIZATION [J].
SHEN, QR ;
SLOSS, DG ;
BERKOWITZ, DB .
SYNTHETIC COMMUNICATIONS, 1994, 24 (11) :1519-1530
[22]  
TSANG R, 1986, J AM CHEM SOC, V108, P2126