Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Total Synthesis of Calothrixins A and B via Oxidative Radical Reaction of Cyclohexenone with Aminophenanthridinedione.

ABSTRACT: Bioactive indolo[3,2-j]phenanthridine alkaloids, calothrixin B and its N-oxide derivative calothrixin A have been synthesized via an oxidative free radical reaction. calothrixin B is generated from the commercially available 2,4,5-trimethoxybenzaldehyde in only 7 steps. The key step in this synthesis is the Mn(OAc)3 mediated oxidative free radical reaction of 9-(benzylamino)phenanthridine -7,10-dione with cyclohexenone to form 12-benzyl-12H-indolo[3,2-j]phenanthridine-7,13-dione.

SUBMITTER: Xu S

PROVIDER: S-EPMC4313744 | biostudies-other | 2014 Sep

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Total Synthesis of Calothrixins A and B via Oxidative Radical Reaction of Cyclohexenone with Aminophenanthridinedione.

Xu Su S Nguyen Thao T Pomilio Irene I Vitale Maria C MC Velu Sadanandan E SE

Tetrahedron 20140901 35

Bioactive indolo[3,2-j]phenanthridine alkaloids, calothrixin B and its N-oxide derivative calothrixin A have been synthesized via an oxidative free radical reaction. calothrixin B is generated from the commercially available 2,4,5-trimethoxybenzaldehyde in only 7 steps. The key step in this synthesis is the Mn(OAc)3 mediated oxidative free radical reaction of 9-(benzylamino)phenanthridine -7,10-dione with cyclohexenone to form 12-benzyl-12H-indolo[3,2-j]phenanthri ...[more]

PMID: 25663720

Similar Datasets

An Expedient Synthesis of Murrayaquinone A via a Novel Oxidative Free Radical Reaction.

Project description:Murrayaquinones A-D is a group of four bioactive carbazole-1,4-dione natural products isolated from the root bark of the plant Murraya eucrestifolia hayata. Murrayaquinone is synthesized in five steps starting from the commercially available 2,4,5-trimethoxybenzaldehyde with an overall yield of 45%. The novelty of this murrayaquinone synthesis is in the use of a Mn(OAc)3 mediated oxidative radical reaction of a N-benzylaminoquinone derivative with 2-cyclohexen-1-one for the late-stage indole ring construction.

| S-EPMC5935454 | biostudies-literature

Total synthesis of pareitropone via radical anion coupling.

Project description:A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.

| S-EPMC2929295 | biostudies-literature

Total Synthesis of Ganoapplanin Enabled by a Radical Addition/Aldol Reaction Cascade.

Project description:The total synthesis of the Ganoderma meroterpenoid ganoapplanin, an inhibitor of T-type voltage-gated calcium channels, is reported. Our synthetic approach is based on the convergent coupling of a readily available aromatic polyketide scaffold with a bicyclic terpenoid fragment. The three contiguous stereocenters of the terpenoid fragment, two of which are quaternary, were constructed by a diastereoselective, titanium-mediated iodolactonization. For the fusion of the two fragments and to simultaneously install the crucial biaryl bond, we devised a highly effective two-component coupling strategy. This event involves an intramolecular 6-exo-trig radical addition of a quinone monoacetal followed by an intermolecular aldol reaction. A strategic late-stage oxidation sequence allowed the selective installation of the remaining oxygen functionalities and the introduction of the characteristic spiro bisacetal structure of ganoapplanin.

| S-EPMC7616391 | biostudies-literature

Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling.

Project description:The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key step, enabled generation of the axial chirality.

| S-EPMC6174078 | biostudies-literature

Total synthesis of aspeverin via an iodine(III)-mediated oxidative cyclization.

Project description:The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product.

| S-EPMC5633934 | biostudies-literature

Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization.

Project description:The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.

| S-EPMC8497573 | biostudies-literature

Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones.

Project description:We report a total synthesis of the pyridine-containing limonoid alkaloid (-)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.

| S-EPMC6499388 | biostudies-literature

Stereoselective Synthesis of Oxazolidin-2-Ones via an Asymmetric Aldol/Curtius Reaction: Concise Total Synthesis of (-)-Cytoxazone.

Project description:Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (-)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.

| S-EPMC7865922 | biostudies-literature

Enantioselective total synthesis of (-)-nardoaristolone B via a gold(I)-catalyzed oxidative cyclization.

Project description:The first enantioselective total synthesis of (-)-nardoaristolone B is accomplished by the implementation of an enantio- and diastereoselective copper(I)-catalyzed conjugate addition/enolate trapping sequence and a gold(I)-catalyzed oxidative cyclization (intermolecular oxidant), employed for the first time in total synthesis.

| S-EPMC4322447 | biostudies-other

Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.

Project description:Medium-ring natural products exhibit diverse biological activities but such scaffolds are underrepresented in probe and drug discovery efforts due to the limitations of classical macrocyclization reactions. We report herein a tandem oxidative dearomatization-ring-expanding rearomatization (ODRE) reaction that generates benzannulated medium-ring lactams directly from simple bicyclic substrates. The reaction accommodates diverse aryl substrates (haloarenes, aryl ethers, aryl amides, heterocycles) and strategic incorporation of a bridgehead alcohol generates a versatile ketone moiety in the products amenable to downstream modifications. Cheminformatic analysis indicates that these medium rings access regions of chemical space that overlap with related natural products and are distinct from synthetic drugs, setting the stage for their use in discovery screening against novel biological targets.

| S-EPMC6242278 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data