88911-35-7

Upstream product

• 114297-54-0 9(O)-methano-Δ^6(9α)-prostaglandin I₁ 11,15-bis-t-butyldimethylsilyl ether 
• 130276-70-9 5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(S)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-1-trimethylsilanyl-pentan-1-one 
• 88931-51-5 isocarbacyclin 
• 136807-37-9 5-[(3aS,5R,6R,6aS)-5-Acetoxy-6-((E)-(S)-3-acetoxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester 
• 163877-58-5 (S)-tert-butyl-dimethyl(oct-1-en-3-yloxy)silane 
• 49826-05-3 (R)-(+)-methyl 2-oxo-1-cyclopentaneacetate 
• 118908-50-2 C₂₀H₂₄O₅ 
• 118908-51-3 C₂₆H₄₆O₄Si 
• 92134-28-6 methyl (1R,5S,6S,7R)-6-tert-butyldimethylsilyloxymethyl-7-tetrahydropyranyloxybicyclo<3.3.0>oct-2-ene-3-pentanoate 
• 92134-31-1 methyl (1R,5S,6R,7R)-6-(3-oxo-(E)-1-octenyl)-7-tetrahydropyranyloxybicyclo<3.3.0>oct-2-ene-3-pentanoate 
• 110456-26-3 (Z)-7-{(1R,2R,3R)-5-Methylene-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester 
• 53232-40-9 (Z)-7-{(1R,2R,3R)-5-Oxo-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester 
• 88911-32-4 5-{(1bS,3R,4R,4aS)-3-(Tetrahydro-pyran-2-yloxy)-4-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-1-oxa-cyclopropa[a]pentalen-5a-yl}-pentanoic acid methyl ester 
• 88911-30-2 5-{(3aS,4R,5R,6aS)-1,2-Dihydroxy-5-(tetrahydro-pyran-2-yloxy)-4-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-octahydro-pentalen-2-yl}-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Diastereoselective total synthesis of isocarbacyclin from L-ascorbic acid

Diastereoselective total synthesis of isocarbacyclin, which features a fused bicyclic key intermediate available from L-ascorbic acid, is described. The key intermediate was prepared in multigram quantities by the Pauson-Khand reaction of L-ascorbic acid-based (R)-4,4-diallyl-2,2-dimethyl-5- (trimethylsilyl)ethynyl-1,3-dioxolane (3), discriminating diastereotopic groups and faces of the geminal allyl substituents.

Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues

A cross metathesis (CM) approach has been successfully applied to introduce fully functionalized ω-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF2α, and the formal syntheses of 15-deoxy-TIC and PGJ2.

Exploration of ω-side chain addition strategies for the syntheses of isocarbacyclin and 15R-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin

We describe alternative access to prostacyclin analogues by means of two ω-side chain addition strategies: Grignard reagent addition to an α,β-unsaturated Weinreb amide, followed by diastereoselective reduction of the corresponding enone system, and imple

IMPROVED SYNTHESIS OF ISOCARBACYCLIN USING REGIOSELECTIVE ALKYLATION OF ALLYLIC ALCOHOLS

Two efficient syntheses of isocarbacyclin (1) have been realized using higly regioselective alkylation of both endo- and exo-allylic alcohols (2 and 3).

AN EFFICIENT SYNTHESIS OF ISOCARBACYCLIN STARTING FROM FURFURAL

Two synthetic routes to isocarbacyclin starting from furfural are described.One route involves the regioselective hydrogenation of the disubstituted olefin in the presence of two other olefinic double bonds, and the other includes the highly regioselective organocopper coupling with the allylic electrophile as a key step.