Synthesis of latanoprost diastereoisomers

被引:12
作者
Obadalová, R [1 ]
Pilarcík, T [1 ]
Slavíková, MF [1 ]
Hájícek, J [1 ]
机构
[1] ZENTIVA VUFB, R&D Synth Grp 2, API Div, CZ-10237 Prague, Czech Republic
关键词
prostaglandins; glaucoma; Corey's alcohol; chiral cyclopentenone; higher-order cuprate; diastereoselective Michael addition;
D O I
10.1002/chir.20116
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new synthesis of latanoprost diastereoisomers is described which utilizes a highly stereoselective Michael addition of higher-order cuprate to a chiral cyclopentenone derived from G-lactone in the crucial skeleton-forming step. Chirality 17:S109-S113, 2005. (c) 2005 Wiley-Liss, Inc.
引用
收藏
页码:S109 / S113
页数:5
相关论文
共 13 条
[1]  
Bindra J. S., 1977, PROSTAGLANDIN SYNTHE
[2]   Studies on the stereoselectivity of osmylation of cis-bicyclo[3.3,0]oct-6-enes [J].
Broom, N ;
OHanlon, PJ ;
Simpson, TJ ;
Stephen, R ;
Willis, CL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (24) :3067-3072
[3]   SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS [J].
COLLINS, PW ;
DJURIC, SW .
CHEMICAL REVIEWS, 1993, 93 (04) :1533-1564
[4]   INTERMEDIATES OF PROSTANOID SYNTHESIS - STEREOSPECIFIC CONVERSION OF (+)-5-BETA-HYDROXYCYCLOPENTEN-2-YL-1-BETA-ACETIC ACID GAMMA-LACTONE INTO (+)-1-BETA-METHOXYCARBONYLMETHYL-2-BETA-3-BETA-(P-NITROBENZYLIDENE)-DIOXYCYCLOPENTAN-5-ONE [J].
FREIMANIS, J ;
GERCA, L ;
TUROVSKIS, I ;
LIEPINS, E ;
LOLA, D ;
MISHNEV, A ;
BUNDULE, M ;
BLEIDELIS, J .
JOURNAL FUR PRAKTISCHE CHEMIE, 1987, 329 (01) :39-48
[5]  
GENET JP, 1995, TETRAHEDRON LETT, V36, P4801
[6]  
GRUBER L, 1974, TETRAHEDRON LETT, V15, P3729
[7]   2-THIENYL(CYANO)COPPER LITHIUM - A LOWER ORDER, STABLE CUPRATE IN A BOTTLE PRECURSOR TO HIGHER-ORDER REAGENTS [J].
LIPSHUTZ, BH ;
KOERNER, M ;
PARKER, DA .
TETRAHEDRON LETTERS, 1987, 28 (09) :945-948
[8]  
NEWTON RF, 1982, PROSTAGLANDINS THROM
[9]   PROSTAGLANDIN SYNTHESES BY 3-COMPONENT COUPLING [J].
NOYORI, R ;
SUZUKI, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :847-876
[10]  
PHARM AB CHINOIN, Patent No. 544899