1-BETA-METHYLTHIENAMYCIN - SOME STEREOCONTROLLED APPROACHES TOWARDS THE KEY INTERMEDIATE

被引:13
作者
GURJAR, MK
BHANU, MN
KHARE, VB
BHANDARI, A
DESHMUKH, MN
RAO, AVR
机构
[1] Indian Institute of Chemical Technology, Hyderabad
关键词
1-BETA-METHYLTHIENAMYCIN; CARBAPENEM ANTIBIOTICS; STEREOSPECIFIC HYDROGENATION; STEREOSELECTIVE HYDROBORATION; ALLYLIC HYDROXYLATION;
D O I
10.1016/S0040-4020(01)96165-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two stereocontrolled approaches towards a precursor of 1 beta-methyl-thienamycin, have been accomplished by involving stereospecific hydrogenation of 13 and stereoselective hydroboration oxidation of 9. The latter compounds were obtained from the easily accessible chiral building block 7. The hydroboration-oxidation approach was extended to 18 in which the optically active 1R- (1-hydroxy ethyl) side-chain was incorporated. The highly stereoselective hydroboration-oxidation reaction of 9 is explained by considering Houk's models.
引用
收藏
页码:7117 / 7128
页数:12
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