162086-59-1Relevant articles and documents
Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction
Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Pugliese, Andrea,Tentori, Francesca
, p. 5122 - 5130 (2017/11/09)
A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopentene- and cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 °C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 °C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.
Achieving Regio- and Enantioselectivity of P450-Catalyzed Oxidative CH Activation of Small Functionalized Molecules by Structure-Guided Directed Evolution
Agudo, Ruben,Roiban, Gheorghe-Doru,Reetz, Manfred T.
body text, p. 1465 - 1473 (2012/09/08)
Directed evolution of the monooxygenase P450-BM3 utilizing iterative saturation mutagenesis at and near the binding site enables a high degree of both regio- and enantioselectivity in the oxidative hydroxylation of cyclohexene-1-carboxylic acid methyl est
Studies aimed at the total synthesis of azadirachtin. A modeled connection of C-8 and C-14 in azadirachtin
Fukuzaki, Takehiro,Kobayashi, Satoshi,Hibi, Takamasa,Ikuma, Yohei,Ishihara, Jun,Kanoh, Naoki,Murai, Akio
, p. 2877 - 2880 (2007/10/03)
(figure presented) Studies on the connection between the right and left segments of azadirachtin are described. The Ireland-Claisen rearrangement of Li-enolate of the modeled ester with dichlorodimethylsilane in toluene afforded the desired limonoid frame