61426-49-1Relevant academic research and scientific papers
Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones
Boyd, Derek R.,Sharma, Narain D.,McIntyre, Peter B. A.,Stevenson, Paul J.,McRoberts, W. Colin,Gohil, Amit,Hoering, Patrick,Allen, Christopher C. R.
, p. 4002 - 4014 (2017/11/22)
Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studies, of anilines and phenols, at the active site of toluene dioxygenase. Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives. (Figure presented.).
Synthesis of trans -2,6-disubstituted cyclohexanones through allylic substitution
Kobayashi, Yuichi,Feng, Chao,Ikoma, Atsushi,Ogawa, Narihito,Hirotsu, Takayuki
supporting information, p. 760 - 763 (2014/03/21)
trans-2,6-Disubstituted cyclohexanones were synthesized with high regio- and stereoselectivity by allylic substitution followed by ozonolysis. Both alkyl and aryl groups were successfully installed to the cyclohexane ring. The stereochemistry of the Ssub
Allylic substitution of esters derived from 2-bromocyclohex-2-enol with aryl copper reagents and synthetic utilization of the derived anti s N2′ products
Ikoma, Atsushi,Kobayashi, Yuichi
, p. 1150 - 1154 (2014/05/20)
Allylic substitution of esters derived from 2-bromocyclohex-2-enol with PhMgBr-based copper reagent was investigated to find high anti S N2′ selectivity with the diethyl phosphate, whereas other esters such as picolinate, acetate, and mesylate resulted in partial racemization or recovery of the starting esters. This protocol was applied to the copper reagent derived from 2-Me-4-MeOC6H3MgBr and CuBr·SMe2 and the olefin part of the anti S N2′ product was cleaved for a synthesis of patchouli alcohol. Georg Thieme Verlag Stuttgart New York.
Overcoming equilibrium issues with carbonyl reductase enzymes
Calvin, Susan J.,Mangan, David,Miskelly, Iain,Moody, Thomas S.,Stevenson, Paul J.
experimental part, p. 82 - 86 (2012/05/31)
We report herein the screening, optimisation and scale up to 100 g of a bioreduction process that employs an in situ product removal (ISPR) technique to overcome the inherent equilibrium problem associated with the coupled-substrate approach to biocatalyt
Total synthesis of echinopines A and B
Nicolaou,Ding, Hanfeng,Richard, Jean-Alexandre,Chen, David Y.-K.
supporting information; experimental part, p. 3815 - 3818 (2010/05/15)
Eohinopines A and B [(+)-1 and (+)-2], two naturally occurring compounds characterized with a unique [3.5.5.7] carbon framework, have been synthesized In both enantiomeric and racemic forms. Their total synthesis Involves a novel intramolecular rhodium-catalyzed cyclopropanation (4 →16) and a samarium dilodide-medlated ring closure (3 → 37).
Cascade palladium-catalyzed direct intramolecular arylation/alkene isomerization sequences: Synthesis of indoles and benzofurans
Yagoubi, Myriam,Cruz, Ana C. F.,Nichols, Paula L.,Elliott, Richard L.,Willis, Michael C.
supporting information; experimental part, p. 7958 - 7962 (2011/01/11)
One route, two cycles: A palladium-catalyzed intramolecular direct arylation reaction combined with an isomerization step provided a straightforward synthetic route to both indoles and benzofurans (see scheme). Isolation and functionalization of intermedi
The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications
Ebner, David C.,Bagdanoff, Jeffrey T.,Ferreira, Eric M.,McFadden, Ryan M.,Caspi, Daniel D.,Trend, Raissa M.,Stoltz, Brian M.
supporting information; experimental part, p. 12978 - 12992 (2010/06/19)
The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.
Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines
-
, (2008/12/08)
Methods are provided for using a compound to treat, for example, endothelial dysfunction including vascular abnormalities. More specifically, methods are described for using an oligosaccharide compound or glycomimetic compound wherein a cyclohexane derivative is incorporated in either.
An enantiocontrolled approach for the synthesis of chiral 3,5-disubstituted 2(1H)-pyridinones
Williams, David R.,Kammler, David C.,Goundry, William R.F.
, p. 555 - 559 (2007/10/03)
An enantioselective route for the convergent synthesis of chiral, nonracemic 5-substituted 3-acyl-2(1H)-pyridinones is reported. Claisen rearrangement provides direct access to the α-branched 2-[4-(tert-butyldimethylsilanoxy)cyclohex-2-enyl]-3-hydroxypropionaldehyde as a key intermediate. The application of mild oxidation conditions facilitates the preparation of a series of 3,5-disubstituted 2(1H)-pyridinones.
Arene cis-dihydrodiols-useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid
Humphreys, Jane L.,Lowes, David J.,Wesson, Karen A.,Whitehead, Roger C.
, p. 5099 - 5108 (2007/10/03)
The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5).
