Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid
@article{Suau2002SynthesisO3, title={Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid}, author={Rafael Suau and Rodrigo Rico and Juan Manuel L{\'o}pez-Romero and Francisco N{\'a}jera and Antonio S{\'a}nchez Ruiz and Francisco Javier Ort{\'i}z-L{\'o}pez}, journal={Arkivoc}, year={2002}, volume={2002} }
Double cyclization of aryloxy-phenyl acetamides is promoted by oxalyl chloride/stannyl chloride and gives 3,4-dioxocularine and aristocularine alkaloids. Rearrangement of the dibenzoxepine ring prior to the second cyclization produces xanthene derivatives. The synthesized cularinoids exhibit significant activity against various tumoral cell lines.
14 Citations
The palladium(0) Suzuki cross-coupling reaction as the key step in the synthesis of aporphinoids
- Chemistry, Biology
- 2004
Synthesis and evaluation of novel oxoisoindoline derivatives as acetylcholinesterase inhibitors
- Chemistry, BiologyMonatshefte für Chemie - Chemical Monthly
- 2014
An efficient synthetic route for the synthesis of novel oxoisoindoline derivatives was described through Ugi reaction of 2-formylbenzoic acids, amines, and isocyanides. All compounds were evaluated…
The chemistry of isoindole natural products
- Chemistry, BiologyBeilstein journal of organic chemistry
- 2013
This review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton, found in its intact or modified form in indolocarbazoles, macrocyclic polyketides, the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloid.
Phosphazene Base-Catalyzed Intramolecular Hydroamidation of Alkenes with Amides.
- Chemistry, BiologyOrganic letters
- 2022
A method for the synthesis of cyclic amides via phosphazene base-catalyzed intramolecular hydroamidation of amide alkenes was developed using a catalytic amount of P4-base and could also be used to synthesize lactam, cyclic urea, and oxazolidinone compounds.
Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
- ChemistryEuropean Journal of Organic Chemistry
- 2020
This is the peer reviewed version of the following article: Deichert, J.A., Mizufune, H., Patel, J.J., Hurst, T.E., Maheta, A., Kitching, M.O., Ross, A.C. and Snieckus, V. (2020), Expedient…
Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids.
- Chemistry, BiologyJournal of chromatography. A
- 2006
Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS.
- Biology, ChemistryPhytochemical analysis : PCA
- 2005
Nine taxa of the genus Sarcocapnos (Fumariaceae) were identified and quantified by GC-MS in nine taxa and the chemotaxonomic significance of the results is discussed.
Nanoscale Biocompatible Structures Generated from Fluorinated Tripodal Phenylenes on Gold Nanoprisms
- ChemistryChemistryOpen
- 2022
Abstract Modification of gold substrates with a stable, uniform and ultrathin layer of biocompatible materials is of tremendous interest for the development of bio‐devices. We present the fabrication…
Determination of Aristocularine Enantiomers by Dispersive Liquid–Liquid Microextraction and Chiral High-performance Liquid Chromatography
- Chemistry
- 2017
ABSTRACT Here is reported a novel analytical approach for the extractive separation and determination of enantiomeric ratios of aristocularine in bovine serum albumin. The results demonstrate…
References
SHOWING 1-10 OF 19 REFERENCES
The isoquinoline alkaloids
- Chemistry, Biology
- 1971
1. ISOQUINOLINE ALKALOIDS - ORIGINS AND DEGREDATION 2. ss-PHENYLETHYLAMINES AND SIMPLE ISOQUINOLINES 2.1 Structures 2.2 Syntheses 2.3 Chemical Properties 2.4 Polymeric Isoquinolines 2.5…
Z:E mixture, 3:2.5); 1 H-NMR δ (CDCl 3 ) Mayor isomer (Z)
- CHCl
OMe), 3.92 (3H, s, OMe), 3.84 (3H, s, OMe), 3.66 (3H, s, NMe); 13 C-NMR δ (CDCl 3 ) 175.2 (C-4)
Ar-H), 6.68 (1H, s, H-α), 4.04 (3H, s, OMe), 3.66 (3H, s, NMe); 13 C-NMR δ
- Ar-H), 7.36-7.16 (4H, m
Orange solid, 0.084 g, 12%; mp 283-90 ºC
- CHCl
Starting products 4a-c were readily prepared by bromination (Br 2 /AcOH) of phenylacetic acid, 3,4-dimethoxyphenylacetic acid and 3,4-methylenedioxy
90) nm; HRMS calcd
- C 15 H 10 O 5 (M + ) m/z 270.0528
Ar-H), 5.70 (1H, s, H-α), 3.89 (3H, s, OMe), 3.20 (3H, s, NMe); 13 C-NMR δ
- CDCl 3 ) 7.28 (1H, d, J=8.4, Ar-H), 7.1-6.9 (4H, m, Ar-H), 6.89 (1H, d, J=8