61898-55-3Relevant academic research and scientific papers
On the total synthesis of (S)-methanophenazine and the formal synthesis of (R)-methanophenazine from a common precursor
Beifuss,Tietze
, p. 9759 - 9763 (2000)
Methanophenazine is a new cofactor from methanogenic archaea. (S)-Methanophenazine has been synthesized from three building blocks, i.e. 2-hydroxy-phenazine, ethyl (R)-3-methylglutarate and (E,E)-farnesyl acetone; a stereodivergent approach from ethyl (R)-3-methylglutarate warrants the formal synthesis of (R)-methanophenazine. (C) 2000 Elsevier Science Ltd.
Highly enantioselective 1,4-conjugate addition of dialkylzinc to α,β-unsaturated lactone catalyzed by diphosphite-copper complexes
Liang, Liang,Su, Liming,Li, Xingshu,Chan, Albert S. C.
, p. 7217 - 7220 (2003)
The 1,4-addition of diethylzinc and dimethylzinc to 5,6-hydro-2H-pyran-2-one using new chiral diphosphite-copper catalysts gave products in up to 98% ee.
Tandem intermolecular alkylation-intramolecular robinson annelation: A novel and stereoselective construction of the octalin skeleton - Expeditious synthesis of (-)-tanabalin
Watanabe, Hidenori,Onoda, Takahiro,Kitahara, Takeshi
, p. 2545 - 2548 (1999)
Tanabalin (1), an insect antifeedant, was synthesized in optically active form employing a known δ-lactone (F) as the only source of chirality. The key step is a tandem intermolecular alkylation-intramolecular Robinson annelation to construct the trans-octalin skeleton.
Total Synthesis of Huperzine R
Nomura, Toshimune,Yokoshima, Satoshi,Fukuyama, Tohru
, p. 119 - 121 (2018/01/17)
A total synthesis of huperzine R was accomplished. Intramolecular cycloaddition of a nitrile oxide and reductive cleavage of the resulting isoxazoline induced sequential cleavage of the C-C and C-O bonds to form the characteristic bicyclic lactam core with an enone moiety. Construction of the butenolide moiety from the enone afforded huperzine R.
Biocatalytic Characterization of Human FMO5: Unearthing Baeyer-Villiger Reactions in Humans
Fiorentini, Filippo,Geier, Martina,Binda, Claudia,Winkler, Margit,Faber, Kurt,Hall, Mélanie,Mattevi, Andrea
, p. 1039 - 1048 (2016/05/19)
Flavin-containing mono-oxygenases are known as potent drug-metabolizing enzymes, providing complementary functions to the well-investigated cytochrome P450 mono-oxygenases. While human FMO isoforms are typically involved in the oxidation of soft nucleophiles, the biocatalytic activity of human FMO5 (along its physiological role) has long remained unexplored. In this study, we demonstrate the atypical in vitro activity of human FMO5 as a Baeyer-Villiger mono-oxygenase on a broad range of substrates, revealing the first example to date of a human protein catalyzing such reactions. The isolated and purified protein was active on diverse carbonyl compounds, whereas soft nucleophiles were mostly non- or poorly reactive. The absence of the typical characteristic sequence motifs sets human FMO5 apart from all characterized Baeyer-Villiger mono-oxygenases so far. These findings open new perspectives in human oxidative metabolism.
Cyclopropanol Methodology in the Synthesis of (4R)- and (4S)-4-Methyltetrahydro-2H-pyran-2-ones. Application in the Synthesis of Insect Pheromones with Methyl-Branched Carbon Skeleton
Mineeva
, p. 341 - 351 (2015/05/04)
A number of chiral methyl-branched building blocks have been synthesized starting from (4S)-4-methyltetrahydro-2H-pyran-2-one, and the possibility for using them for the preparation of mealworm beetle, rhinoceros beetle, and earth-boring dung beetle phero
Ferrocene phosphane-carbene ligands in Cu-catalyzed enantioselective 1,4-additions of Grignard reagents to α,β-unsaturated carbonyl compounds
Csizmadiová, Jana,Me?iarová, Mária,Almássy, Ambroz,Horváth, Branislav,?ebesta, Radovan
, p. 47 - 52 (2013/06/27)
Chiral ferrocene phosphane-carbenes are good ligands for the copper-catalyzed 1,4-addition of Grignard reagents to various Michael acceptors. The products were obtained in high enantiomeric purity (up to e.r. = 95:5) and excellent regioselectivity (r.r. =
(4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one in the synthesis of polyfunctional compounds with the methyl-branched carbon skeleton
Mineeva
, p. 253 - 258 (2013/07/25)
A simple and efficient asymmetrical synthesis was performed of a convenient bifunctional building block, methyl (R)-5,5-dimethoxy-3-methylpentanoate and its (S)-enantiomer. The possibility was shown of its application to the synthesis of insect pheromones.
Asymmetric conjugate addition of grignard reagents to pyranones
Mao, Bin,Fa?anás-Mastral, Martín,Feringa, Ben L.
supporting information, p. 286 - 289 (2013/03/13)
An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as β-alkyl substituted aldehydes or β-bromo-γ-alkyl substituted alcohols with excellent regio-and stereoselectivity.
Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes
Verendel, J. Johan,Li, Jia-Qi,Quan, Xu,Peters, Byron,Zhou, Taigang,Gautun, Odd R.,Govender, Thavendran,Andersson, Pher G.
, p. 6507 - 6513 (2012/06/29)
Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. Copyright
