73252-53-6Relevant academic research and scientific papers
Tubulin-binding dibenz[c,e]oxepines: Part 2.1Structural variation and biological evaluation as tumour vasculature disrupting agents
Rossington, Steven B.,Hadfield, John A.,Shnyder, Steven D.,Wallace, Timothy W.,Williams, Kaye J.
, p. 1630 - 1642 (2017/02/26)
5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascular shu
Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation
Punganuru, Surendra R.,Aviraboina, Sivaprasad,Srivenugopal, Kalkunte S.
, p. 375 - 378 (2016/07/06)
A concise stereoselective total synthesis of (+)-monocerin has been accomplished using cross metathesis, tandem dihydroxylation-SN2 cyclisation and intramolecular alkoxycarbonylation as key steps. Cross-metathesis of 2-iodo-3,4,5-trimethoxyvinylbenzene and (R)-hepten-4-ol, followed by tandem dihydroxylation-SN2 cyclisation generated a tri-substituted tetrahydrofuran ring. Finally, the dihydroisocoumarin was obtained by an intramolecular alkoxycarbonylation. In this paper, we have developed an expedient operationally simple Pd(OAc)2/bathocuproine catalysed alkoxycarbonylation under atmospheric pressure of carbon monoxide. The catalytic system developed here can be useful for the synthesis of various dihydroisocoumarins and phthalides.
Diversity-oriented synthesis of intensively blue emissive 3-hydroxyisoquinolines by sequential Ugi four-component reaction/reductive heck cyclization
Moni, Lisa,Valentini, Gianluca,Riva, Renata,Deniβen, Melanie,Müller, Thomas J. J.
supporting information, p. 753 - 762 (2015/04/27)
A convergent approach to highly functionalized 3-hydroxyisoquinolines is reported. The key steps are an Ugi multicomponent reaction and a subsequent intramolecular reductive Heck reaction; these can also be performed as a one-pot procedure. The structures
Synthesis of indole-derived allocolchicine congeners through Pd-catalyzed intramolecular C-H arylation reaction
Sitnikov, Nikolay S.,Kokisheva, Antonina S.,Fukin, Georgy K.,Neud?rfl, J?rg-Martin,Sutorius, Hannah,Prokop, Aram,Fokin, Valery V.,Schmalz, Hans-Günther,Fedorov, Alexey Yu.
, p. 6481 - 6492 (2016/02/18)
The synthesis of several new heterocyclic structural analogs of the natural antimitotic agent allocolchicine is reported. As a key step an intramolecular Pd-catalyzed C-H arylation reaction was used to close the seven-membered ring fused with two electron
Total synthesis of six 3,4-unsubstituted coumarins
Gao, Wenqing,Li, Qingyong,Chen, Jian,Wang, Zhichao,Hua, Changlong
, p. 15613 - 15623 (2014/01/17)
In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins-7-hydroxy- 6,8-dimethoxycoumarin (isofraxidin), 7-hydroxy-6-methoxycoumarin (scopoletin), 6,7,8-trimethoxycoumarin, 6,7-dimethoxycoumarin (scoparone), and 7,8-dihydroxycoumarin (daphnetin) and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5- dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4- dihydroxybenzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxybenzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin.
1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, a novel compound class with potent chemoreversal activity
Hung, Hsin-Yi,Ohkoshi, Emika,Goto, Masuo,Nakagawa-Goto, Kyoko,Lee, Kuo-Hsiung
, p. 7726 - 7729 (2013/02/23)
1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, which share a fragment from (±)-3′-O-4′-O-bis(3,4-dimethoxycinnamoyl)-cis- khellactone (DMDCK) and 3′R,4′R-disubstituted-2′,2′- dimethyldihydropyrano[2,3-f]chromone (DSP), exhibited remarkable chemoreversa
Aromatic iodination using N-iodosaccharin in room temperature ionic liquids
Bailey, Lindsey,Handy, Scott T.
experimental part, p. 2413 - 2414 (2011/05/09)
More reactive iodination conditions have been developed that combine the use of room temperature ionic liquids with N-iodosaccharin. Using these reaction conditions, even very modestly activated arenes such as toluene can be iodinated in good yield under very mild conditions.
A [2 + 2 + 2]-cycloaddition approach toward 6-oxa-allocolchicinoids with apoptosis-inducing activity
Nicolaus, Norman,Strauss, Susanne,Neudoerfl, Joerg-Martin,Prokop, Aram,Schmalz, Hans-Guenther
supporting information; experimental part, p. 341 - 344 (2009/09/05)
(Chemical Equation Presented) Following an A → ABC strategy, a new synthesis of 6-oxa-allocolchicinoids was developed exploiting a microwave-promoted Co- or Rh-catalyzed intramolecular [2 + 2 + 2]-cycloaddition (alkyne cyclotrimerization) as a key step. T
Asymmetric synthesis of (S)-(-)-N-acetylcolchinol via Ullmann biaryl coupling
Broady, Simon D.,Golden, Michael D.,Leonard, John,Muir, James C.,Maudet, Mickael
, p. 4627 - 4630 (2008/02/06)
A modified Ziegler Ullmann coupling process has been developed as the key step in an effective synthesis of (S)-(-)-N-acetylcolchinol, analogues of which are selective vascular targeting agents with potential importance in cancer chemotherapy. Asymmetric induction is achieved by enamide hydrogenation using FerroTANE catalysts.
[5]Helicenes by tandem radical cyclisation
Harrowven, David C.,Nunn, Michael I.T.,Fenwick, David R.
, p. 7345 - 7347 (2007/10/03)
A new and rapid approach to [5]helicenes is described. A central feature is the use of a sequential, non-reducing radical cyclisation reaction of (Z,Z)-1,4-bis(2-iodostyryl)benzene derivatives, viz. 3→1, mediated by tributyltin hydride.
