871095-01-1

Upstream product

• 871095-00-0 tert-butyl((1R,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-((E)-4-m-tolylbut-1-enyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane 
• 934968-46-4 tert-butyldimethyl{(2R,3R,3aS,6aS)-5-[5-(tetrahydro-2H-pyran-2-yloxy)pentyl]-3-[(E)-4-m-tolylbut-1-enyl]-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy}silane 
• 934968-25-9 (3a'S,4'R,5'R,6a'R)-5,5-dimethyl-4'-[(E)-4-m-tolylbut-1-enyl]hexahydro-1'H-spiro([1,3]dioxane-2,2'-pentalen)-5'-ol 
• 934968-26-0 (3aS,4R,5R,6aR)-5-hydroxy-4-[(E)-4-m-tolylbut-1-enyl]hexahydropentalen-2(1H)-one 
• 934968-29-3 (3aS,4R,5R,6aR)-5-(tert-butyldimethylsilyloxy)-4-[(E)-4-m-tolylbut-1-enyl]hexahydropentalen-2(1H)-one 
• 934968-34-0 (E)-[(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl]-2-{(3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-[(E)-4-m-tolylbut-1-enyl]hexahydropentalen-2(1H)ylidene} acetate 
• 934968-38-4 (1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl-2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl} acetate 
• 934968-41-9 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethanol 
• 934968-45-3 2-{(3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-[(E)-4-m-tolylbut-1-enyl]-1,3a,4,5,6,6a-hexahydropentalen-2-yl}ethyl 4-methylbenzenesulfonate 
• 286440-95-7 1-[(5-bromopentyloxy)methyl]-4-methoxybenzene 
• 871095-06-6 5-(3-m-tolylpropylthio)-1-phenyl-1H-tetrazole 
• 871094-99-4 5-(3-m-tolylpropylsulfonyl)-1-phenyl-1H-tetrazole 
• 871095-04-4 (3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one 
• 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 

Relevant academic research and scientific papers

Asymmetric synthesis of 3-oxa-15-deoxy-16-(m-tolyl)-17,18,19,20- tetranorisocarbacyclin and its neuroprotective analogue 15-deoxy-16-(m-tolyl)- 17,18,19,20-tetranorisocarbacyclin based on the conjugate addition-azoalkene- asymmetric olefination strategy

A fully stereocontrolled synthesis of 3-oxa-15-deoxy-16-(m-tolyl)17,18,19, 20-tetranorisocarbacyclin (3-oxa-15-deoxy-TIC, 7b) and a formal one of 15-deoxy-16-(w-tolyl)-17,18,19,20-tetranorisocarbacyclin (15- deoxy-TIC, 7a) are described. 15Deoxy-TIC is sp

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.