54396-60-0

Upstream product

• 73588-55-3 methyl (5Z,13E)-9α,15-bis(dimethyl-t-butylsilyloxy)-11-oxoprosta-5,13-dienoate 
• 73579-11-0 methyl (5Z,13E)-9α,15-bis(dimethyl-t-butylsilyloxy)-11α-hydroxyprosta-5,13-dienoate 
• 98598-77-7 methyl(8,9-cis-9,12-trans)-9-t-butyldimethylsilyloxy-11-oxo-15β-hydroxy-prosta-5(Z),13(E)-dienoate-11-ethylene acetal 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 98582-47-9 2,3-trans-3,4-cis-2-(hydroxy-methyl)-3-(prop-2-enyl)-4-t-butyldimethylsilyloxy cyclopentanone ethylene acetal 
• 98582-48-0 2,3-trans-3,4-cis-2-(methyl-acetyloxy)-3-(prop-2-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-49-1 2,3-trans-3,4-cis-2-(methyl-acetyloxy)-3-(methyl-formyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-45-7 2,3-trans-3,4-cis-2-ethoxycarbonyl-3-(prop-2-enyl)-4-nitroxy-cyclopentanone ethylene acetal 
• 98582-51-5 (Z)-7-[(6S,7R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid 
• 98582-52-6 2,3-trans-3,4-cis-2-(hydroxy-methyl)-3-(-methoxycarbonyl-hex-2(Z)-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-50-4 (Z)-7-[(6S,7R,8S)-6-Acetoxymethyl-8-(tert-butyl-dimethyl-silanyloxy)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid 
• 98582-53-7 2,3-trans-3,4-cis-2-formyl-3-(6-methoxycarbonyl-hex-2(Z)-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-44-6 2,3-trans-3,4-trans-2-ethoxycarbonyl-3-(prop-2-enyl)-4-p-toluen-sulfonyloxy cyclopentanone ethylene acetal 
• 98582-54-8 methyl-(8,9-cis-9,12-trans)-9-t-butyldimethylsilyloxy-11,15-dioxo-prosta-5(Z),13(E)-dienoate-11-ethylene acetal 

Relevant academic research and scientific papers

A Short and Efficient Total Synthesis of (+/-) Prostaglandin D2 Methyl Ester involving a New Method for the Cleavage of a Dimethyl-t-butylsilyl Ether

Baeyer-Villiger oxidation of the bicycloheptanone (4; R = SiMe2But) afforded a mixture of isomeric lactones (5) and (6), the minor component (6) being conveniently removed by selective hydrolysis.Reduction of the lactone (5) by di-isobutylaluminium hydride gave the corresponding lactol (8).Conversion of (8) into the 9α-silyloxyprostanoid (10) was performed so as to minimise silyl group migration.Oxidation to (10) gave the ketone (12) but the hindered siloxy-group at C-9 was extremely resistant to cleavage by the usual reagents.Satisfactory deprotection of (12) was achieved by treatment with aqueous HF in acetonitrile to give (+/-)-prostaglandin D2 methyl ester (14) and (+/-)-15-epi-prostaglandin D2 methyl ester (15).The high 'silicophilicity' and low acidity of HF make it the reagent of choice for cleavage of silyl ethers under mildly acidic conditions.

PROSTAGLANDINS: TOTAL SYNTHESIS OF PGD2 "via" 1,3 CYCLOPENTANEDIONE

A practical total synthesis of PGD2 starting from an acyclic precursor is reported.A novel efficient inversion of stereochemistry at C9 tosylate group "via" a SN2 displacement by tetrabutylammonium nitrate is described.