88911-35-7

Upstream product

• 119008-13-8 (3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-pentalen-1-one 
• 119008-14-9 (3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-hexahydro-pentalen-1-one 
• 118908-52-4 5-{(2R,3aR,4R,5R,6aS)-2-Benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-1-oxo-octahydro-pentalen-2-yl}-pentanoic acid methyl ester 
• 95205-45-1 5-{(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid 
• 88931-51-5 isocarbacyclin 
• 88911-34-6 5-[(3aR,5S,6S,6aR)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester 
• 95205-48-4 (1R^*,5S^*,6R^*,7R^*)-3-acetoxymethyl-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)bicyclo<3.3.0>oct-2-ene 
• 125089-83-0 (1R^*,5S^*,6R^*,7R^*)-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)bicyclo<3.3.0>oct-2-ene-3-pentanal 
• 95205-50-8 (1R^*,5S^*,6R^*,7R^*)-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)-3-(5-hydroxypentyl)bicyclo<3.3.0>oct-2-ene 
• 95205-46-2 (1R^*,5S^*,6R^*,7R^*)-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)-3-hydroxymethylbicyclo<3.3.0>oct-2-ene 
• 95205-42-8 (1R^*,5S^*,6R^*,7R^*)-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)bicyclo<3.3.0>oct-2-ene-3-carbaldehyde 
• 95205-54-2 (1S^*,2S^*,3S^*,4R^*)-4-tert-butyldimethylsilyloxy-3-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)-1-hydroxymethyl-2-(3-hydroxypropyl)-cyclopentane 
• 82304-78-7 (2S,3S,4S)-2-Allyl-4-(tert-butyl-dimethyl-silanyloxy)-3-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopentanone 
• 95205-53-1 (2R^*,3S^*,4R^*)-2-allyl-4-tert-butyldimethylsilyloxy-3-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)-1-methylenecyclopentane 

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.

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

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.

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).

THE INTRAMOLECULAR THERMAL ENE REACTION ROUTE TO (+)-9(O)-METHANO-Δ6(9α)-PGI1

(+)-9(O)-Methano-Δ6(9α)-PGI1, a more potent carbon analog than carbacyclin, has been synthesized from the Corey lactone by utilizing the intramolecular thermal ene reaction as a key step.