A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles

[Display omitted] •A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds. 2...

Full description

Saved in:
Bibliographic Details
Published in:Journal of fluorine chemistry 2020-08, Vol.236, p.109554, Article 109554
Main Authors: Gromova, M.A., Kharitonov, Yu.V., Politanskaya, L.V., Tretyakov, E.V., Shults, E.E.
Format: Article
Language:English
Subjects:
2Н-chromenes
Benzofuran
Benzofurans
Coupling (molecular)
Cross coupling
Cross-coupling-cyclization
Diterpenes
Fluorinated heterocycles
Fluorination
Fluorine
Heterocyclic compounds
Isopimaric acid
Optical activity
Substitutes
Terpenoid allene
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] •A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds. 2,3-Butadienes have become valuable building blocks in the synthesis of various heterocyclic compounds. The Pd-catalyzed cross-coupling and cyclization reaction of N-(2,3-butadienyl)carboxamide of isopimaric acid with fluorine-substituted 2-iodophenols proceeds with the formation of optically active fluorinated benzofuran and benzopyrane derivatives of isopimaric acid. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid moiety and several fluorinated benzoannelated heterocycles.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2020.109554