26097-34-7Relevant academic research and scientific papers
Chiral Synthesis of (-)-Colletol Based on Palladium-Catalyzed Reductive Cleavage of Alkenyloxiranes with Formic Acid
Shimizu, Isao,Omura, Tetsuya
, p. 1759 - 1760 (1993)
Total synthesis of (-)-colletol was achieved using palladium-catalyzed hydrogenolysis of optically active (E)-4,5-epoxy-2-alkenoates to (E)-5-hydroxy-2-alkenoates with formic acid as a key step for preparation of the intermediate hydroxy ester segments.
Base-Induced Heterochiral Dimerization of an Oxiranyl Carbaldimine: Stereoselective Synthesis of a Highly Functionalized Aziridine
Alickmann, Dirk,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
, p. 1527 - 1530 (2001)
matrix presented Treatment of the oxiranyl carbaldimine with base (LDA or LDA/KOtBu) leads in an one-step procedure to the polyfunctionalized aziridine. This highly diastereoselective reaction is explained by a new type of an Aza-Darzens reaction, in which one enantiomer of the starting material is deprotonated to form an oxiranyl anion, which attacks the imine carbon atom of the other enantiomer (mutual kinetic resolution by double diastereofacial selection).
Epoxidation of crotyl alcohol using Ti-containing heterogeneous catalysts: Comments on the loss of Ti by leaching
Davies, Lucinda J.,McMorn, Paul,Bethell, Donald,Bulman Page, Philip C.,King, Frank,Hancock, Frederick E.,Hutchings, Graham J.
, p. 319 - 327 (2001)
The leaching of Ti from the redox molecular sieve TS-1 is compared and contrasted with Ti leaching from Ti-Alβ, Ti-MCM-41, and a Ti-xerogel under both batch and continuous flow reaction conditions for the oxidation of crotyl alcohol with hydrogen peroxide. The product distributions for the catalysts are similar, with epoxide being formed initially and, subsequently, the secondary reaction products of the triol and ether diols. Ti leaching is more pronounced under continuous flow conditions and the order of stability is TS-1 > Ti-Alβ > Ti-MCM-41 > Ti-xerogel, for both continuous flow and batch reaction conditions. TS-1 leaching is shown to be caused by the reaction of triol with TS-1 in the presence of hydrogen peroxide. A possible mechanism in which the triol byproduct chelates the Ti and breaks the Ti-O-Si framework bonds, leading in turn to the formation of a Ti species in solution, is proposed. The soluble Ti species is found to be an active homogeneous catalyst giving triol as the major product from crotyl alcohol. Under batch reaction conditions, it is possible that an equilibrium is established between the solution Ti species and Ti on the catalyst surface. This equilibrium is perturbed when continuous flow conditions are used, and this leads to increased Ti leaching.
EFFECT OF METAL HYDRIDE AND SILICA GEL ON THE SHARPLESS ASYMMETRIC EPOXIDATION
Zhi-min, Wang,Wei-shan, Zhou,Guo-giang, Lin
, p. 6221 - 6224 (1985)
The reaction time of asymmetric epoxidation of allylic alcohol was greatly reduced when a catalytic amount of both metal hydride and silica gel was occured in the Sharpless reagent.
Multigram synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine
Burk, Matthew,Wilson, Nolan,Herzon, Seth B.
, p. 3231 - 3234 (2015)
The synthesis of 1-O-acetyl-3-O-(4-methoxybenzyl)-4-N-(9-fluorenylmethoxycarbonyl)-4-N-methyl-l-pyrrolosamine (7), which constitutes a protected form of the N,N-dimethyl-l-pyrrolosamine residues found within the antiproliferative bacterial metabolites (-)
A computational study of vicinal fluorination in 2,3- Difluorobutane: Implications for conformational control in alkane chains
Fox, Stephen J.,Gourdain, Stephanie,Coulthurst, Anton,Fox, Clare,Kuprov, Ilya,Essex, Jonathan W.,Skylaris, Chris-Kriton,Linclau, Bruno
, p. 1682 - 1691 (2015)
A comprehensive conformational analysis of both 2,3-difluorobutane diastereomers is presented based on density functional theory calculations in vacuum and in solution, as well as NMR experiments in solution. While for 1,2-difluoroethane the fluorine gauc
Apoptosis-inducing effect of epolactaene derivatives on BALL-1 cells
Kuramochi, Kouji,Matsui, Rie,Matsubara, Yasuaki,Nakai, Junko,Sunoki, Takashi,Arai, Satoshi,Nagata, Seigo,Nagahara, Yukitoshi,Mizushina, Yoshiyuki,Ikekita, Masahiko,Kobayashi, Susumu
, p. 2151 - 2161 (2006)
Epolactaene, a neuritogenic compound in human neuroblastoma SH-SY5Y, induces apoptosis in a human leukemia B-cell line, BALL-1. The apoptosis-inducing activities of 34 epolactaene derivatives, including those of the newly synthesized α-alkyl-α,β-epoxy-γ-l
Selective epoxidations involving anionic peroxotungsten compounds generated in situ on layered double hydroxides with various polarities
Sels, Bert F.,De Vos, Dirk E.,Jacobs, Pierre A.
, p. 8557 - 8560 (1996)
WO42-exchanged LDH catalyses the epoxidation of simple olefins and allylic alcohols. Substrate reactivity, chemo- and regioselectivity vary markedly with the polarity of the peroxotungstate environment.
A facile method for promoting activities of vanadium-schiffbase complex anchored on organically modified MCM-41 in epoxidation reaction
Parida,Singha, Sudarshan,Sahoo
, p. 40 - 47 (2010)
A heterogeneous catalytic system (V-MCM-41) displays a most pronounced efficiency with NaHCO3 as co-catalyst and H2O2 as oxidant in a CH3CN medium at room temperature towards epoxidation reaction.
First total synthesis of fuzanins C, D and their analogues as anticancer agents
Kumar, S. Naveen,Pavan Kumar, C. H. N. S. Sai,Srihari,Kancharla, Sravani,Srinivas, Kolupula,Shrivastava, Shweta,Naidu,Jayathirtha Rao
, p. 8365 - 8375 (2014)
The first total synthesis of fuzanins C and D, isolated from the culture supernatant of Kitasatospora sp. IFM10917, is described. Key features of this synthetic strategy involve the use of Sharpless asymmetric epoxidation, dihydroxylation, Mitsunobu reaction and Julia-Kocienski olefination. The total synthesis reported herein also confirmed the absolute configuration of fuzanin D. The optical rotations of synthesized fuzanin D and natural product were opposite in sign, leading to a revision of the reported structure as its enantiomer which is further confirmed by molecular modeling studies. In addition, we also synthesized the analogues of fuzanins C, D containing the quinoline nucleus. All of the synthesized compounds were screened for anticancer activity on four cell lines and found to be potent against HT29 colon cancer cell lines, whereas they were found to be less potent against cervical and breast cancer cell lines.
