186895-45-4Relevant academic research and scientific papers
One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope
Devlin, Rory,Jones, David J.,Mcglacken, Gerard P.
supporting information, p. 5223 - 5228 (2020/07/14)
A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.
Copper(i)-catalysed transfer hydrogenations with ammonia borane
Korytiaková, Eva,Thiel, Niklas O.,Pape, Felix,Teichert, Johannes F.
, p. 732 - 735 (2017/01/13)
Highly Z-selective alkyne transfer semihydrogenations and conjugate transfer hydrogenations of enoates can be effected by employing a readily available and air-stable copper(i)/N-heterocyclic carbene (NHC) complex, [IPrCuOH]. As an easy to handle and potentially recyclable H2 source, ammonia borane (H3NBH3) is used.
Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa
Kantee, Kawalee,Rukachaisirikul, Vatcharin,Tadpetch, Kwanruthai
, p. 3505 - 3509 (2016/07/15)
Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.
Stereoselective total synthesis of (3S,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol, (3S,5S)-alpinikatin, and its diastereoisomers
Venkatesham, Kunuru,Purushotham Reddy, Sudina,Chinnababu, Baggu,Suresh Babu, Katragadda
, p. 1307 - 1314 (2015/09/28)
Stereoselective synthesis of the diarylheptanoids, (3S,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol (1), (3S,5S)-alpinikatin (3), and their diastereoisomers (2 and 4, resp.), was achieved from readily available 4-hydroxybenzaldehyde. The synthetic sequenc
The first stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)-1,7-bis(4-hydroxyphenyl)hept-6-en-3-ol, through two different approaches
Kashanna, Jajula,Jangili, Paramesh,Kumar, Rathod Aravind,Das, Biswanath
, p. 1666 - 1671 (2012/11/07)
The stereoselective total synthesis of a naturally occurring bioactive diarylheptanoid, (3R,6E)-1,7-bis(4-hydroxyphenyl)hept-6-en-3-ol, has been accomplished starting from 4-hydroxybenzaldehyde through two different approaches involving Wittig olefination
Highly active iridium(i) complexes for the selective hydrogenation of carbon-carbon multiple bonds
Bennie, Linsey S.,Fraser, Calum J.,Irvine, Stephanie,Kerr, William J.,Andersson, Shalini,Nilsson, Goeran N.
supporting information; experimental part, p. 11653 - 11655 (2011/12/05)
New iridium(i) complexes, bearing a bulky NHC/phosphine ligand combination, have been established as extremely efficient hydrogenation catalysts that can be used at low catalyst loadings, and are compatible with functional groups which are often sensitive to more routinely employed hydrogenation methods.
Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe
Busscher, Guuske F.,Lefort, Laurent,Cremers, Jozef G.O.,Mottinelli, Marco,Wiertz, Roel W.,Lange, Ben De,Okamura, Yutaka,Yusa, Yukinori,Matsumura, Kazuhiko,Shimizu, Hideo,De Vries, Johannes G.,De Vries, Andre H.M.
experimental part, p. 1709 - 1714 (2010/10/20)
Two routes for the preparation of an N-aryl β-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh- or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the β-keto ester which yielded the β-amino ester in high yield and 97% ee. Subsequent copper-catalyzed N-arylation gave the target compound.
β1- and β2-adrenoceptor antagonist activity of a series of para- substituted N-isopropylphenoxypropanolamines
Louis, Simon N.,Nero, Tracy L.,Iakovidis, Dimitri,Colagrande, Felicia M.,Jackman, Graham P.,Louis, William J.
, p. 919 - 937 (2007/10/03)
To further explore the structure-activity relationships of β- adrenoceptor (β-AR) antagonists, a series of 25 para-substituted N- isopropylphenoxy-propanolamines were synthesised, nine of which are new compounds. All have been examined for their ability to antagonise β1-ARs in rat atria and β2-ARs in rat trachea. Substitution in the para-position of the phenyl ring is thought to confer β3-specificity and the selectivity of these compounds for the β1-AR ranges from 1.5-234. None of the compounds tested were selective for the β2-AR. Of the 25 compounds studied, 22 had reasonable (pA2 > 7) potencies for the rat β1-AR. Only compound 1 displayed reasonable (pA2 > 7) potency for the rat β2-AR. Twenty two compounds were used as the training set for comparative molecular field analysis (CoMFA) of antagonist potency (pA2) at the rat β1- and β2-ARs. The inclusion of a number of additional physical characteristics improved the QSAR analysis over models derived solely using the CoMFA electrostatic and steric fields. The final models predicted the β1- and β2-AR potency of the compounds in the training set with high accuracy (r2 = 0.93 and 0.86 respectively). The final β1-AR model predicted the β1-potencies of two out of the three test compounds, not included in the training set, with residual PA2 values 2-AR model (residual pA2 values -0.38).
