122552-67-4

Upstream product

• 107657-42-1 (4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 59995-47-0 (R)-(+)-4-hydroxy-2-cyclopentenone 
• 178034-11-2 (3R,5S)-(+)-3-acetoxy-5-(trimethylacetyloxy)cyclopent-1-ene 
• 178034-12-3 (1S,4R)-4-hydroxycyclopent-2-enyl 2,2,2-trimethylacetate 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 865302-28-9 (3R,5S)-(+)-3-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(trimethylacetyloxy)cyclopent-1-ene 
• 817210-68-7 (1S,4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-ol 

Downstream Products

• 865302-29-0 (3S,4R)-(+)-2-bromo-3-ethenyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-1-ene 
• 122552-70-9 (E)-(3R,3aR,5S,6aR,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-9a-methyl-4-methylene-3,3a,4,5,6,6a,7,8,9,9a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one 
• 122552-69-6 {(1R,2S)-2-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(1-iodo-vinyl)-5-oxo-cyclopent-(E)-ylidenemethyl]-2-methyl-cyclopentyl}-acetaldehyde 
• 122552-72-1 (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one 
• 123517-71-5 C₃₂H₄₀O₄Si 
• 122576-95-8 (E)-(3R,3aS,6aR,9aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one 
• 122552-80-1 (E)-(1R,3R,3aS,6aR,9aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-1,9a-dimethyl-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-1-ol 
• 122552-71-0 C₃₆H₄₂N₂O₄SSi 
• 865302-38-1 C₆₀H₉₆NO₁₁PSi 
• 865302-32-5 (4R,5R)-(+)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-5-(2Z-octenyl)-α-[(1R,2R)-1,2-epoxy-6-(4-methoxyphenylmethoxy)hexyl]cyclopent-2-enemethanol 
• 865302-33-6 (3R,4R)-(+)-2E-2-[(2R,3R)-2,3-epoxy-7-(4-methoxyphenylmethoxy)hept-1-enyl]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)-cyclopentanone 
• 865302-36-9 (2R,3R)-3-Z-[(4R,5R)-5-(2Z-octenyl)-2-oxo-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopentylidenemethyl]oxirane-2-butanoic acid 
• 865302-34-7 (3R,4R)-(+)-2E-2-[(2R,3R)-2,3-epoxy-7-hydroxyhept-1-enyl]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)-cyclopentanone 
• 865302-35-8 (3R,4R)-(+)-2E-2-[(2R,3R)-2,3-epoxy-7-oxohept-1-enyl]-4-[(1,1-dimethylethyl)diphenylsilyloxy]-3-(2Z-octenyl)-cyclopentanone 

Relevant academic research and scientific papers

Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC

(Chemical Equation Presented) A total synthesis of the naturally occurring hydroxy ketone PEIPC 1, a compound that plays a role in endothelial activation in atherosclerosis, has been completed via a triply convergent preparation of a protected EI derivative 13 from 3,5-diacetoxycyclopentene 7, pentane-1,5-diol, and vinyllithium, using Sharpless epoxidation and enzymatic resolution as key steps. Final coupling with lyso-PC 16 and silyl group deprotection gave PECPC 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC.

SYNTHETIC STUDIES ON OPHIOBOLINS

The tricyclic ketone 14, an ophiobolin analogue lacking only the C-ring side chain, was synthesized in optically active form; the key step was the intramolecular NiCl2/CrCl2 mediated coupling of 10 to yield 11.