871095-04-4

Upstream product

• 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 
• 118375-00-1 (1S,2R,3R,5R)-7,7-(2,2-Dimethyltrimethylenedioxy)-3-hydroxybicyclo<3.3.0>octan-2-carbonsaeure-methylester 
• 117624-93-8 (1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 104172-98-7 (3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)hexahydropentalen-2(1H)-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 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 

Downstream Products

• 871094-96-1 (3aS,4S,5R,6aR)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydropentalen-2(1H)-one 
• 871094-94-9 (1R,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalene-1-carbaldehyde 
• 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 
• 871095-05-5 ((1S,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)methanol 
• 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 
• 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 
• 871094-95-0 (3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl trifluoromethanesulfonate 
• 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 
• 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 
• 78919-13-8 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octa-3-ylidene)-pentanoic acid 
• 82889-99-4 5Z-Iloprost 

Relevant academic research and scientific papers

An alternative synthesis for iloprost via a key bicyclic aldehyde intermediate

An alternative synthesis for iloprost has been accomplished in 14 steps via a convergent synthesis starting from commercially available (?)-Corey lactone diol. The syntheses employ a new and key chiral bicyclic aldehyde (4) intermediate, which is primed for attachment of the required α-side chain and ω-side chain.

Iloprost key intermediate and preparation method thereof

The invention belongs to the field of medicine synthesis, and relates to an iloprost key intermediate and a preparation method thereof. Specifically the method comprises: by taking corey lactone diolrepresented by a formula III as an initial raw material, protecting hydroxy, carrying out condensation with phosphate ester, carrying out Collines oxidation and Wittig-Horner reaction to generate an intermediate represented by a formula VII, carrying out double bond reduction and selective deprotection to generate an intermediate represented by a formula IX, carrying out Dess-Martin oxidation to generate aldehyde represented by a formula X, carrying out condensation on the aldehyde represented by the formula X and a ylide side chain represented by a formula XI to obtain a compound representedby a formula XII, and carrying out selective carbonyl protection to obtain a key intermediate represented by a formula II-1. Compared with other routes, the method of the invention has the advantagesthat reaction steps are greatly reduced, starting materials are cheap and easy to obtain, the process is simple, convenient and easy to control, the total yield is high, industrial production is easy,and the like.

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.