51014-26-7

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carboxylic acid-(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester is used as an intermediate in the synthesis of Prostaglandin E2 (P838610) for its potent biological activities. Prostaglandin E2 is the most common and biologically active prostaglandin found in mammals, playing crucial roles in various physiological processes, including inflammation, pain, and blood flow regulation. The synthesis of this prostaglandin is of great importance in the development of pharmaceuticals targeting these conditions.

Upstream product

• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 31753-00-1 [1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 

Downstream Products

• 38344-08-0 (5Z)-bimatoprost acid 

Relevant academic research and scientific papers

A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.

Process for the stereoselective reduction of α,β-unsaturated ketones

A process for the preparation of α,β-unsaturated alcohols of general formula (I), wherein R means an alkyl group of 1-4 carbon atoms, or benzoyloxy group optionally substituted with a phenyl group; R1means a hydrogen atom or an alkyl group of 1-4 carbon atoms, R2means a hydrogen atom or an alkyl group of 1-4 carbon atoms; R3means an alkyl group of 1-6 carbon atoms optionally substituted by phenyl group or cycloalkyl group of 5-7 carbon atoms; or a phenoxy group optionally substituted by a halogen atom, or a cycloalkyl group of 5-7 carbon atoms; R4means a hydrogen atom or a halogen atom whereby at α,β-unsaturated ketones of general formula (II) wherein the meanings of R, R1, R2, R3, and R4are as given above—is diastereoselectively reduced with a borohydride type compound in an aprotic solvent, in the presence of an inorganic substance dissolublein the reaction mixture and having particle size from 0.01 micrometer to 10000 micrometer and optionally from the resulting mixture of epimeric α,β-unsaturated alcohols of general formula (I) and (III) meanings of R, R1, R2, R3, and R4are as given above—the α,β-unsaturated alcohol of general formula (I) is separated by methods known.