Cargando…

Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A

[Image: see text] A synthetic approach to a functionalized ABC-tricyclic framework of calyciphilline A-type alkaloids, a building block toward this class of alkaloids, is reported. The key synthetic steps involve a radical cyclization to form the hydroindole system and piperidine ring closure throug...

Descripción completa

Detalles Bibliográficos
Autores principales:	Marquès, Clàudia, Diaba, Faïza, Gómez-Bengoa, Enrique, Bonjoch, Josep
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2022
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881646/ https://www.ncbi.nlm.nih.gov/pubmed/35862855 http://dx.doi.org/10.1021/acs.joc.2c01171

Ejemplares similares

The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N
por: Shvartsbart, Artem, et al.
Publicado: (2015)

Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical
por: Ibrahim, Ahmad A., et al.
Publicado: (2014)

Catalytic enantioselective synthesis of carbocyclic and heterocyclic spiranes via a decarboxylative aldol cyclization
por: Inanaga, Kazato, et al.
Publicado: (2020)

Stereocontrolled Total Synthesis of (−)‐Stemaphylline
por: Varela, Ana, et al.
Publicado: (2017)

On the proposed structures and stereocontrolled synthesis of the cephalosporolides
por: Tlais, Sami F, et al.
Publicado: (2012)

Stereocontrolled Synthesis and Functionalization of Cyclobutanes and Cyclobutanones
por: Secci, Francesco, et al.
Publicado: (2013)

Stereocontrolled Synthesis of 2‐Fluorinated C‐Glycosides
por: Sadurní, Anna, et al.
Publicado: (2018)

Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone
por: Isoda, Motoyuki, et al.
Publicado: (2022)

Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core
por: Park, Sangbin, et al.
Publicado: (2022)

Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
por: Shigeoka, Daisuke, et al.
Publicado: (2013)

Base-Mediated Nitrophenyl Reductive Cyclization for the Synthesis of Hexahydro-2,6-methano-1-benzazocines
por: Rodríguez, Laura G., et al.
Publicado: (2022)

Enantioselective Total Synthesis of (−)-Himalensine A via a Palladium and 4-Hydroxyproline Co-catalyzed Desymmetrization of Vinyl-bromide-tethered Cyclohexanones
por: Kučera, Roman, et al.
Publicado: (2023)

Independent Control of Elastomer Properties through Stereocontrolled Synthesis
por: Bell, Craig A., et al.
Publicado: (2016)

Synthesis of μ-ABC Tricyclic Miktoarm Star Polymer via Intramolecular Click Cyclization
por: Shingu, Tomoki, et al.
Publicado: (2018)

A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin
por: Valdez Pérez, Luis F., et al.
Publicado: (2022)

Efficient syntheses of (–)-crinine and (–)-aspidospermidine, and the formal synthesis of (–)-minfiensine by enantioselective intramolecular dearomative cyclization
por: Du, Kang, et al.
Publicado: (2017)

Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes
por: Konno, Tsutomu, et al.
Publicado: (2012)

Stereocontrolled Synthesis of α-Xylofuranosides Using a Conformationally Restricted Donor
por: Zhang, Li, et al.
Publicado: (2018)

Stereocontrolled Total Synthesis of Bastimolide B Using Iterative Homologation of Boronic Esters
por: Fiorito, Daniele, et al.
Publicado: (2022)

Stereocontrolled Synthesis of Fluorinated Isochromans via Iodine(I)/Iodine(III) Catalysis
por: Häfliger, Joel, et al.
Publicado: (2022)

Aerobic Oxidative N-Heterocyclic Carbene-Catalyzed Formal [3+3] Cyclization for the Synthesis of Tetrasubstituted Benzene Derivatives
por: Bacaicoa, Sara, et al.
Publicado: (2022)

Solid-phase synthesis and properties of stereocontrolled boranophosphate/phosphate and phosphorothioate/phosphate chimeric oligouridylates
por: Sato, Kazuki, et al.
Publicado: (2023)

Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade
por: Brandstätter, Marco, et al.
Publicado: (2019)

Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
por: Itoh, Tomoki, et al.
Publicado: (2019)

Cyclization of interlocked fumaramides into β-lactams: experimental and computational mechanistic assessment of the key intercomponent proton transfer and the stereocontrolling active pocket
por: Martinez-Cuezva, Alberto, et al.
Publicado: (2020)

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
por: Enders, Dieter, et al.
Publicado: (2012)

Synthesis of Isocoumarins with Different Substituted Patterns via Passerini–Aldol Sequence
por: Ma, Guan-Hua, et al.
Publicado: (2014)

Very Recent Advances in Vinylogous Mukaiyama Aldol Reactions and Their Applications to Synthesis
por: Cordes, Martin, et al.
Publicado: (2019)

Synthesis of Natural (−)-Antrocin and Its Enantiomer via Stereoselective Aldol Reaction
por: Angamuthu, Venkatachalam, et al.
Publicado: (2020)

Synthesis of Selenoesters via Aldol Condensation and/or Conjugate Reduction and Their Antiviral Activities
por: Boateng, Alex, et al.
Publicado: (2022)

Stereocontrolled Synthesis of 1,4‐Dicarbonyl Compounds by Photochemical Organocatalytic Acyl Radical Addition to Enals
por: Goti, Giulio, et al.
Publicado: (2018)

P-stereocontrolled synthesis of oligo(nucleoside N3′→O5′ phosphoramidothioate)s – opportunities and limitations
por: Radzikowska, Ewa, et al.
Publicado: (2020)

Stereocontrolled synthesis of some novel functionalized heterocyclic amino ester and amide derivatives with multiple stereocenters
por: Semghouli, Anas, et al.
Publicado: (2023)

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine
por: Regni, Alessio, et al.
Publicado: (2023)

Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
por: Ubaidullaev, A. U., et al.
Publicado: (2022)

Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
por: Matsumura, Kunihiro, et al.
Publicado: (2018)

Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones
por: Meazza, Marta, et al.
Publicado: (2018)

Efficient and Stereocontrolled Synthesis of 1,2,4-Trioxolanes Useful for Ferrous Iron-Dependent Drug Delivery
por: Fontaine, Shaun D., et al.
Publicado: (2014)

Solid-Phase Stereocontrolled Synthesis of Oligomeric P-Modified Glycosyl Phosphate Derivatives Using the Oxazaphospholidine Method
por: Sato, Kazuki, et al.
Publicado: (2021)

Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation
por: Ďurina, Lukáš, et al.
Publicado: (2021)

Cannot write session to /tmp/vufind_sessions/sess_d3ps5lobp8huc9ihvlbl8rfut5