60623-67-8

Upstream product

• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Downstream Products

• 39182-59-7 (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxyoct-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 26054-67-1 (-)-7α-hydroxy-6β-(3α-hydroxy-1E-octenyl)-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 51388-75-1 (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol 
• 551-11-1 dinoprost 
• 38562-01-5 dinoprost tromethamine 
• 363-24-6 dinoprostone 
• 13345-50-1 prostaglandin A₂ 
• 23782-33-4 (1SR,5RS,6RS,7RS)-7-hydroxy-6-<(3SR)-3-hydroxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 
• 23782-33-4 (1SR,5RS,6RS,7RS)-7-hydroxy-6-<(3RS)-3-hydroxyoct-1(E)-enyl>-2-oxabicyclo<3.3.0>octan-3-one 
• 73070-15-2 (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3,3'-dibenzoate 
• 73078-82-7 Benzoic acid (R)-1-{(E)-2-[(3aR,4R,5R,6aS)-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]-vinyl}-hexyl ester 
• 73078-82-7 Benzoic acid (S)-1-{(E)-2-[(3aR,4R,5R,6aS)-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]-vinyl}-hexyl ester 
• 73089-63-1 (3'R)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3'-benzoate 
• 73070-13-0 (3'S)-3α,5α-Dihydroxy-2β-(3'-hydroxy-trans-1'-octenyl)cyclopentane-1α-acetic acid γ-lactone 3'-benzoate 

Relevant academic research and scientific papers

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.

PROSTANOIDS. XXXII. SYNTHESIS OF (+)-PROSTAGLANDIN F2α

Natural prostaglandin F2α was obtained from cyclopentadiene monoxide.The key stages of the synthesis included the following: Optical resolution of (+/-)-trans-2-carboxymethylcyclopent-3-en-1-ol with the transformation of its (-)-enantiomer into (-)-cis-2-oxabicyclooct-6-en-3-one and then into (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclooctan-3-one; selective oxidation of the latter by the DMSO-(COCl)2 system; condensation of the intermediate (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclooctan-3-one with dimethyl 2-oxoheptylphosphonate under the conditions of phase-transfer catalysis with the production of (-)-7α-hydroxy-6β-(3-oxo-1E-octenyl)-cis-2-oxabicyclooctan-3-one; conversion of the latter into (+)-PGF2α by standard methods.