176166-15-7

Upstream product

• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 

Downstream Products

• 828295-36-9 4-Nitro-benzoic acid (1R,6S)-2-chloro-6-hydroxy-cyclohex-2-enyl ester 
• 187837-20-3 (1S,6S)-2-Chloro-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-cyclohex-2-enol 
• 1569135-06-3 (1S,2R)-2,3-dichlorocyclohex-3-enol 
• 1498378-66-7 (1S,2R)-2-azido-3-chlorocyclohex-3-enol 
• 1498378-67-8 (1S,4S)-4-azido-3-chloro-3-cyclohexen-1-ol 
• 1569135-02-9 (1S,2R)-2,3-dichlorocyclohex-3-en-1-yl sulfochloridate 
• 1431975-48-2 (+)-(1S,2R)-1-acetoxy-2-bromo-3-chlorocyclohex-3-ene 
• 1392229-39-8 (4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-3-chlorocyclohex-2-en-1-one 
• 1392229-29-6 (4S,5S)-3-chloro-4,5-dihydroxycyclohex-2-enone 
• 426206-55-5 {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane] 
• 1228121-64-9 (1S,2S)-1-benzyloxy-3-chlorocyclohex-3-en-2-ol 
• 1228121-63-8 (1S,2S)-2-benzyloxy-3-chlorocyclohex-3-en-1-ol 
• 828295-37-0 trans-(1S,2R)-1,2-dihydroxy-3-chlorocyclohex-3-ene 
• 929619-83-0 trans-(1S,2R)-1,2-diacetoxy-3-chloro-5-bromocyclohex-3-ene 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene oxides and of a substituted oxepine, via dihydrobenzene oxide intermediates. A rapid total racemization of the substituted benzene 2,3-oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. Reduction of a substituted arene oxide to yield a racemic arene hydrate was observed. Arene hydrates have also been synthesised, in enantiopure form, from the corresponding dihydroarene oxide or trans-bromoacetate precursors. Biotransformation of one arene hydrate enantiomer resulted in a toluene-dioxygenase catalysed cis-dihydroxylation to yield a benzene cis-triol metabolite. The Royal Society of Chemistry 2013.

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.

Cycloalkenyl halide substitution reactions of enantiopure arene cis-tetrahydrodiols with boron, nitrogen and phosphorus nucleophiles

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands. Copyright

A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277

The structure, 5, assigned to the resorcylic acid lactone L-783,290 has been prepared for the first time and in a modular fashion using a Heck reaction to link the readily available fragments 8 and 14. Chemoenzymatic methods were used to prepare the latte

Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers

Enantiopure trans-dihydrodiols have been obtained by a chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites, obtained by dioxygenase-catalysed arene cis-dihydroxylation at the 2,3-bond of monosubstituted benzene substrates. This gen

Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds

A series of chiral α-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclohexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of α- chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented.

A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A.

An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.

A chemoenzymatic synthesis of the 12-membered macrolide (-)-cladospolide A

The enantiomerically pure cis-1,2-dihydrocatechol 7, which is obtained by microbial oxidation of chlorobenzene, has been converted, via a sequence of reactions including ring-closing metathesis and Yamaguchi lactonisation steps, into the natural product (-)-cladospolide A (1).

Chemoenzymatic synthesis of arene oxides and trans-dihydrodiols from cis-dihydrodiols of monosubstituted benzenes

cis-Dihydrodiol bacterial metabolites of monosubstituted benzenes are used in the chemoenzymatic synthesis of the corresponding arene oxide and trans-dihydrodiol mammalian metabolites.