Regioselection Switch in Nucleophilic Addition to Isoquinolinequinones: Mechanism and Origin of the Regioselectivity in the Total Synthesis of Ellipticine.

Ellipticines Isoquinolines

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
17 06 2022
Historique:
pubmed: 17 2 2022
medline: 22 6 2022
entrez: 16 2 2022
Statut: ppublish

Résumé

Ellipticine was synthesized in six steps and 20% global yield starting from the readily available 2,5-dimethoxy isoquinoline. Unprecedented regioselective control of the nucleophilic attack on the isoquinoline-5,8-dione is first described. Investigation of the possible pathways of this transformation through density functional theory calculations reveals unexpected

Identifiants

DOI: 10.1021/acs.joc.1c02952 PMID: 35171607
pubmed: 35171607
doi: 10.1021/acs.joc.1c02952
doi:

Substances chimiques

Ellipticines 0
Isoquinolines 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

7610-7617

Auteurs

Joaquim A M Castro (JAM)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.
ORCID: 0000-0003-2863-6839

Bruno K Serikava (BK)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.

Christian R S Maior (CRS)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.

Fabrício F Naciuk (FF)

Brazilian Biosciences National Laboratory, Brazilian Center for Research in Energy and Materials, Campinas, SP 13083-970, Brazil.

Silvana A Rocco (SA)

Brazilian Biosciences National Laboratory, Brazilian Center for Research in Energy and Materials, Campinas, SP 13083-970, Brazil.

Carolina B P Ligiéro (CBP)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.

Nelson H Morgon (NH)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.

Paulo C M L Miranda (PCML)

Institute of Chemistry, University of Campinas-UNICAMP, P.O. Box 6154, Campinas, SP 13083 970, Brazil.
ORCID: 0000-0002-6418-3614

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Classifications MeSH

questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérocycliques 3 noyaux › Carbazoles › Ellipticines › Regioselection Switch in Nucleophilic Addition...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Isoquinoléines › Regioselection Switch in Nucleophilic Addition...