86853-73-8

Upstream product

• 87701-83-5 3-oxabicyclooctenone 
• 82134-77-8 (3aR,6aS)-1-Hydroxy-hexahydro-cyclopenta[c]furan-4-one 
• 82093-33-2 C₉H₁₂O₄ 
• 77189-14-1 1-oxo-1,3,3a,6a-tetrahydrocyclopentafuran 
• 68882-71-3 2-(hydroxymethyl)cyclopent-2-enone 
• 160023-09-6 (3aS,4S,6aR)-4-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one 
• 187262-21-1 (3aS,6aR)-5-Chloro-tetrahydro-cyclopenta[c]furan-1,4-dione 
• 57445-90-6 pent-4-ene-1,3-diol 
• 127658-18-8 (3aS,4S,5S,6aR)-4-Benzyloxy-1-oxo-hexahydro-cyclopenta[c]furan-5-carboxylic acid 
• 1040919-32-1 (1R,2S)-2-(hydroxymethyl)-N-[(1R)-phenylethyl]-cyclopent-3-ene-1-carboxamide 
• 1361318-14-0 (3aS,4S,5S,6aR)-5-bromo-4-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one 
• 127658-19-9 (3aS,4R,6aR)-4-Benzyloxy-hexahydro-cyclopenta[c]furan-1-one 
• 184376-29-2 (S)-3-(benzyloxy)pent-4-en-1-ol 
• 155690-33-8 (S)-3-hydroxy-4-pentenyl triphenylmethyl ether 

Downstream Products

• 72581-31-8 sarkomycin 

Relevant academic research and scientific papers

Trapping of Cyclopentadienone as a 4? Component in Diels-Alder Reactions with Ethyl Acrylate: a Simple Synthesis of (+/-)-Sarkomycin

The ability of cyclopentadienone to act as the diene counterpart in Diels-Alder reactions was demonstrated through the isolation of the cycloadduct with ethyl acrylate, which was utilized as the starting point for an expeditious synthesis of (+/-)-sarkomycin.

Sarkomycin a methyl esters and functionalized cyclopentane blocks for brefeldin a

Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A were synthesized starting from diastereoisomeric (1R,2S)-and (1S,2R)-2-hydroxymethyl-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamides. Pleiades Publishing, Ltd., 2012.

Synthesis of enantiomeric cyclosarcomycins

Based on chiral cyclopentene blocks 2 and 3, enantiomeric cyclosarcomycins 4 and 5 were obtained and characterised.

An integrated chemoenzymatic synthesis of enantiopure (-)-(1R,5S)-cyclosarkomycin: A sarkomycin precursor

A five-step chemoenzymatic synthesis of (-)-(1R,5S)-cyclosarkomycin 2 has been achieved starting from commercial racemic bicycloheptenone 3. The strategy developed involved - as key steps - an enantioselective microbiologically catalyzed Baeyer-Villiger oxidation followed by a chemical regioselective epoxide ring opening.

Diastereoselective iodocarbocyclization reaction of 2- or 3-oxy-4-pentenylmalonate derivatives

1,2- Or 1,3-asymmetric induction in the iodocarbocyclization reaction of 4-pentenylmalonate derivatives having a stereogenic center at an allylic or a homoallylic position has been investigated. The iodocarbocyclization reactions of 3-oxy-4-pentenylmalonate derivatives proceeded with high cis-selectivity through stereoelectronic control of the oxygenated substituent at an allylic position. In the reaction of (S)-2-siloxy-4-pentenylmalonate, an excellent diastereoselectivity was achieved through the utilization of double stereodifferentiation with a chiral titanium catalyst. Furthermore, as an application of the present reaction, the asymmetric syntheses of cyclosarkomycin and a synthetic intermediate of brefeldin A from optically pure 2- and 3-oxy-4-pentenylmalonate derivatives are also described.

DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES: APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS

The iodocarbocyclization of 4-pentenylmalonate 1 having a substituent at the 2 or 3 position effectively proceeded by treating 1 with I2 and Ti(OtBu)4 in the presence of CuO.Stereoelectronic effect of the substituent at allylic position on diastereoselect

A NEW APPROACH TO CYCLOPENTANE ANNULATED COMPOUNDS VIA 1-(CYCLOPENT-1-ENYLCARBONYL)VINYLPHOSPHONATES, AND SYNTHESIS AND SYNTHETIC APPLICATION OF α-DIETHOXYPHOSPHORYL-Δα,β-BUTENOLIDES

Fused ring systems, containing two or three five-membered rings, were constructed by utilizing 1-(cyclopent-1-enylcarbonyl)vinylphosphonates which function as versatile annulating agents.Facile synthesis of α,β-carbocyclic fused γ-lactones was provided by

ASYMMETRIC DIELS-ALDER REACTIONS: EPC-SYNTHESIS OF A STABLE SARKOMYCIN PRECURSOR (CYCLOSARKOMYCIN)

The first synthesis of enantiomerically pure cyclosarkomycin, a stable, crystaline precursor of the antitumor agent sarkomycin is reported.Key steps are an asymmetric Diels-Alder reaction of the (E)-3-bromoacrylate of (R)-pantolactone and introduction of oxygen funtionality via elimination/β-addition.The synthesis of cyclosarkomycin was accomplished in 9 steps in 17 percent overall yield.