871095-00-0

Upstream product

• 620-23-5 m-tolyl aldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 118375-00-1 (1S,2R,3R,5R)-7,7-(2,2-Dimethyltrimethylenedioxy)-3-hydroxybicyclo<3.3.0>octan-2-carbonsaeure-methylester 
• 131375-63-8 5-(4-methoxybenzyloxy)-1-pentanol 
• 50556-03-1 3-m-tolyl-acrylic acid ethyl ester 
• 111171-94-9 3-(m-methylphenyl)-1-propanol 
• 111-29-5 1 ,5-pentanediol 
• 871094-98-3 tert-butyl((1S,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-(trityloxymethyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane 
• 871094-95-0 (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate 
• 871095-05-5 ((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol 
• 871094-96-1 (3aS,4S,5R,6aR)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydropentalen-2(1H)-one 
• 116896-28-7 [(3a'S,4'S,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalen]-4'-yl]methanol 
• 127708-13-8 methyl (3a'S,4'R,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carboxylate 

Downstream Products

• 871095-02-2 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanoic acid 
• 871095-07-7 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal 
• 871095-01-1 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol 

Relevant academic research and scientific papers

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.

Access to isocarbacyclin derivatives via substrate-controlled enolate formation: Total synthesis of 15-deoxy-16-(m-tolyl)-17,18,19,20- tetranorisocarbacyclin

(Chemical Equation Presented) We describe a convergent and flexible synthesis of 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15-deoxy-TIC), a simple isocarbacyclin derivative. The synthesis takes advantage of two key step reactions: a regioselective deprotonation of the described ketone under substrate control which is then trapped, as the enol triflate, to generate the C6-C9α endocyclic double bond, followed by an sp2-sp3 Pd-catalyzed cross-coupling reaction (C5-C6) with a suitable primary alkyl Grignard reagent. Introduction of the C13-C14 (E)-double bond in the ω-side chain is performed by the Julia-Kocienski olefination.