20224-38-8

Upstream product

• 278-06-8 quadricyclo[2.2.1.0.0]heptane 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 

Downstream Products

• 542-92-7 cyclopenta-1,3-diene 
• 1571-60-4 (E)-Ethene-1,2-diol 
• 24587-76-6 (5-exo,6-exo)-5,6-dibenzoyloxybicyclo<2.2.1>hept-2-ene 
• 23067-44-9 2exo,3exo-bis-(toluene-4-sulfonyloxy)-5-norbornene 
• 144874-60-2 (3aRS,6RS,6aRS)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one 

Relevant academic research and scientific papers

Novel carbocyclic nucleoside containing a cyclopentyl ring and uracil

A carbocyclic analogue of uridine, (±)-1-[t-2,t-3-dihydroxy-c-4- (hydroxymethyl)-r-1-cyclopentylmethyl]-1,2,3,4-tetrahydropyrimidine-2,4- dione (13), was synthesized with a view to studying its structure-activity relationships.

Synthesis of (+/-)-Carbocyclic Analogue of Spirohydantoin Nucleoside

Synthesis of (+/-)-carbocyclic spirohydantoin derivatives of (+)-hydantocidin is described.The pivotal step in the synthesis is spirohydantoin ring construction from cyclopentanone 9.Using the Bucherer-Bergs condition predominately gave the epi-carbocyclic analogue 10, whereas the alternative spiroring formation method through α-aminonitrile 13 provided the carbocyclic analogue 2 after deprotection.

Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides

Carbocyclic C-nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors-properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1′, orthogonal functionalization of position 5′, and efficient inversion of stereochemistry at position 2′. Newly prepared carbocyclic C-analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.

Stereoselective cyclotrimerization of enantiopure iodonorbornenes catalyzed by Pd nanoclusters for C 3 or C 3 v symmetric syntris(norborneno)benzenes

(Figure presented) C3 or C3v symmetric enantiopure syn-tris(norborneno)benzenes with various functional groups were synthesized through Pd-catalyzed cyclotrimerization of enantiopure iodonorbornenes. The generality of Pd-catalyzed cyclotrimerization for syn-tris(norborneno)benzenes were well-demonstrated.

One-pot rhodium(I)-catalyzed hydroboration of alkenes: Radical conjugate addition

B-Alkylcatecholboranes, prepared by rhodium-(I)-catalyzed hydroboration of alkenes, are suitable radical precursors for conjugate addition to activated olefins. This procedure proved to be particularly useful for the control of the regio- and chemoselectivity of such tandem processes. Enantioselective hydroboration has also been successfully coupled with radical chain reaction in a one-pot process.

Highly asymmetric enzymatic hydrolysis and transesterification of meso-bis(acetoxymethyl)- and bis(hydroxymethyl)cyclopentane derivatives: An insight into the active site model of Rhizopus delemar lipase

Rhizopus delemar lipase (RDL)-catalysed hydrolysis of meso-1,3-bis(acetoxymethyl)cyclopentane derivatives (7, 12) and Pseudomonas fluorescens lipase (PFL)-catalysed hydrolysis of 7 afforded the chiral monoacetates (15, 16) of > 99% ee. In explanation of these high enantioselectivities of RDL, the simple box-type active site model of enzyme was tentatively proposed. On the other hand, PFL-catalysed transesterification of meso-bis-(hydroxymethyl)cyclopentane (6) afforded (+)-16 of > 99% ee. The obtained (+) and (-)-16 were converted into the natural carbocyclic nucleoside(-)-aristeromycin (25), respectively.

C-Nucleosides. Part 2. Preparation of 2-thiazole-4-carboxamide ('Carbocyclic' Tiazofurin) and its Antipode

Benzyl 6β-aminopenicillanate 1β-oxide 9c underwent N-acylation with (1R*,2S*,3R*,4R*)-2,3-dibenzoyloxy-4-(benzoyloxymethyl)cyclopentanecarbonyl chloride 11b - assembled in nine steps from trinorbornadiene - to give a mixture of the penicillins 10d and 13c

Rose-Bengal-Sensitized Photooxidation of Quadricyclane. A Cycloaddition of Singlet Oxygen

Quadricyclane was photooxygenated with singlet oxygen generated under Rose-Bengal-sensitized conditions to a dioxetane, which in turn gave 2-cyclopentene-1,4-dicarbaldehyde and 5-norbornene-cis-2,3-exo-diol.For the mechanism to form the dioxetane, an involvement of a electrocyclic process is proposed.

The Oxidation of Norbornadiene and Some Derivatives using Pseudomonas sp.

Norbornadiene is oxidized by a Pseudomonad to give the diol (2) (35percent) while 7-phenylnorbornadiene furnishes 3-norbornadienylcyclohexa-3,5-diene-1,2-diol (10) (41percent) on incubation with the same organism; cyclization reactions involving the acetonide (15) have been investigated.