Synthesis of latanoprost diastereoisomers

Chirality

Volumn 17, Issue SUPPL., 2005, Pages

  Obadalová, Iva ^a   Pilarčík, Tomáš ^a   Slavíková, Markéta ^a   Hájíček, Josef ^a  

^a Zentiva Prague   (Czech Republic)

Author keywords

Chiral cyclopentenone; Corey's alcohol; Diastereoselective Michael addition; Glaucoma; Higher order cuprate; Prostaglandins

Indexed keywords

COPPER DERIVATIVE; CYCLOPENTENONE; LACTONE; LATANOPROST;

CHIRALITY; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; MICHAEL ADDITION; PRIORITY JOURNAL; REDUCTION; STEREOISOMERISM; WITTIG REACTION;

EID: 21844444261     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20116     Document Type: Conference Paper

References (13)

1. Resul B, Stjernchantz J, No K, Liljebris C, Selén G, Astin M, Karlsson M, Bito LZ. Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents. J Med Chem 1993;36:243-248.
2. Bindra JS, Bindra R. Prostaglandin synthesis. New York: Academic Press; 1977.
3. Newton RF, Roberts SM (editors). Prostaglandins and thromboxanes. London: Butterworth; 1982.
4. Noyori R, Suzuki M. Prostaglandin syntheses by three-component coupling. Angew Chem Int Ed Engl 1984;23:847-876.
5. Collins PW, Djuric SW. Synthesis of therapeutically useful prostaglandin and prostacyclin analogues. Chem Rev 1993;93:1533-1564.
6. EP Appl 544899 (Pharmacia AB and CHINOIN).
7. WO 02/096898 (Resolution Chemicals Limited and Cascade Biochem Limited).
8. Gruber L, Tömösközi I, Major E, Kovács G. Stereoselective conversion of (+)-cis-2-oxabicyclo [3.3.0] oct-6-en-3-one into methyl R-(+)-7-(3-hydroxy-5-oxocyclopentenyl)-5-cis-heptenoate. Tetrahedron Lett 1974;15:3729-3730.
9. Freimanis J, Gerca L, Turovskis I, Liepinš E, Lola D, Mishnev A, Bundule M, Bleidelis J. Stereospecific conversion of (+)-5β-hydroxy- cyclopenten-2-yl-1β-acetic acid γ-lactone into (+)-1β- methoxycarbonylmethyl-2β,3β-(p-nitrobenzylidene)dioxycyclopentan-5- one. J Prakt Chem 1987;329:39-48.
10. Broom N, O'Hanlon PJ, Simpson TJ, Stephen R, Willis CL. Studies on the stereoselectivity of osmylation of cis-bicyclo[3.3.0]oct-6-enes. J Chem Soc Perkin Trans 1 1995:3067-3072.
11. Genêt JP, Ratovelomanana-Vidal V, Caño de Andrade MC, Pfister X, Guerreiro P, Lenoir JY. Practical asymmetric hydrogenation of β-keto esters at atmospheric pressure using chiral Ru(II) catalysts. Tetrahedron 1995;36:4801-4804.
12. Lipshutz BH, Koerner M, Parker DA. 2-Thienyl(cyano)copper lithium. A lower order, stable "cuprate in a bottle" precursor to higher order reagents. Tetrahedron Lett 1987;28:945-948.
13. WO 02/090324 (Yonsung Fine Chemical Co.). Chem Abstr 2002; 137:352820.