The synthesis of gem-cyclopentyl substituted glutarates via the oxidative ring contraction of 2-acetylcyclohexanones

被引:2
作者
Challenger, S [1 ]
Derrick, A [1 ]
Silk, TV [1 ]
机构
[1] Pfizer Global Res & Dev, Sandwich CT13 9NJ, Kent, England
关键词
oxidative ring-contraction; hydrogen peroxide; preparation of cyclopentyl substituted glutarates;
D O I
10.1081/SCC-120012979
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A two stop synthesis of differentially protected gem.-cyclopentyl glutarates has been developed from 2-acetylcyclohexanone and acrylates. The key step involves an oxidative ring contraction reaction with hydrogen peroxide. The methodology has been used to prepare intermediates used in the preparation of the atriopeptidase inhibitor candoxatril.
引用
收藏
页码:2911 / 2918
页数:8
相关论文
共 12 条
[1]  
BRUSON HA, Patent No. 2466926
[2]   Stereoselective synthesis of a candoxatril intermediate via asymmetric hydrogenation [J].
Challenger, S ;
Derrick, A ;
Mason, CP ;
Silk, TV .
TETRAHEDRON LETTERS, 1999, 40 (11) :2187-2190
[3]  
CHALLENGER S, Patent No. 391673
[4]  
CHALLENGER S, Patent No. 5166406
[5]  
DANILEWICZ JC, Patent No. 0342850
[6]  
HAWKINS EGE, 1973, J CHEM SOC P1, V19, P2169
[7]  
JAMES K, 1993, PERSPECT MED CHEM, P45
[8]  
KRYSHTAL GV, 1979, SYNTHESIS-STUTTGART, P107
[9]   On the alpha,alpha;alpha 'alpha '-bis-[tetramethyle]-adipic acid. A case of ring narrowing by oxidation. [J].
Mannich, C .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1941, 74 :1007-1014
[10]   STEREOCHEMICAL STUDIES .8. FURTHER-STUDIES OF STEREOCHEMICAL EFFECTS ON THE COURSE OF OXIDATION OF ALPHA-ACYLOCTAHYDRONAPHTHALENONES [J].
MIDDLETON, S ;
STOCK, LE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (11) :2467-2476