301834-98-0

Upstream product

• 88462-65-1 (+/-)-4-[(3-trifluoromethyl)phenoxy]-1-butyne-3-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 301834-96-8 (3R)-4-[3-(trifluoromethyl)phenoxy]-3-hydroxy-1-butyne 
• 443361-68-0 Methanesulfonic acid (S)-1-(3-trifluoromethyl-phenoxymethyl)-prop-2-ynyl ester 
• 63212-88-4 (3-trifluoromethylphenoxy)acetaldehyde diethyl acetal 
• 63212-89-5 (3-trifluoromethylphenoxy)acetaldehyde 
• 98-17-9 3-Trifluoromethylphenol 
• 301834-95-7 (R)-4-[3-(trifluoromethyl)phenoxy]-1-butyne-3-yl butyrate 

Downstream Products

• 1190883-19-2 (Z)-7-((1R,2R,3R)-3-[(tert-butyldimethylsilanyl)oxy]2-((E)-3-((tert-butyldimethylsilanyl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)-5-oxo-cyclopentyl)hept-5-enoic acid isopropyl ester 

Relevant academic research and scientific papers

Rh(I)-Catalyzed 1,4-Conjugate Addition of Alkenylboronic Acids to a Cyclopentenone Useful for the Synthesis of Prostaglandins

An efficient and trans-diastereoselective Rh(I)-catalyzed 1,4-conjugate addition reaction of alkenylboronic acids and a homochiral (R)-4-silyloxycyclopentenone useful for the synthesis of derivatives of prostaglandins E and F is described for the first time. The reaction functions under mild conditions and is particularly rapid (≤6 h) under low power (50 W) microwave irradiation at 30 °C in MeOH in the presence of a catalytic amount of KOH. Under these conditions, 3 mol % of [RhCl(COD)]2 is typically required to produce high yields. The method also functions without microwave irradiation at 3 °C in the presence of a stoichiometric amount of KOH. Under these conditions, only 1.5 mol % of [RhCl(COD)]2 is needed, but the reaction is considerably slower. The method accepts a range of aryl- and alkyl-substituted alkenylboronic acids, and its utility has been demonstrated by the synthesis of PGF2α (dinoprost) and tafluprost.

Synthesis of the potent antiglaucoma agent, travoprost

A commercial synthesis of the antiglaucoma agent, travoprost 2, is described. A total of 22 synthetic steps are required to provide the single enantiomer prostanoid, with the longest linear sequence being 16 steps from 3-hydroxybenzotrifluoride. The route is based upon a cuprate-mediated coupling of the single enantiomer vinyl iodide 13 and the tricyclic ketone 5, of high stereochemical purity, to yield the single isomer bicyclic ketone 15. A Baeyer - Villiger oxidation provides the lactone 16 as a crystalline solid, thus limiting the need for chromatographic purification. DIBAL-H reduction, Wittig reaction, esterification, and silyl group deprotection complete the synthesis of travoprost.

An Enantioconvergent Synthesis of (R)-4-Aryloxy-1-butyne-3-ols for Prostanoid Side Chains

The single enantiomer title alcohols, useful as co-side chain precursors for pharmaceutically important prostaglandin analogues were synthesised from the corresponding racemic alcohols by a convenient 4-step sequence. After enzymatic acylation of the alco

Process for the preparation of prostaglandin precursors

A propargylic alcohol, enriched in the (R)-enantiomer, has the formula wherein R is C1-4 alkoxy, halogen, or C1-4 alkyl optionally substituted by OH or halogen. This is prepared by the steps of: (a) enantioselective (R)-esterification of the racemic alcohol using any acyl donor and a first enzyme; (b) removal of the untreated (S)-alcohol; and (c) enantioselective hydrolysis of the (R)-ester, using a second enzyme.