Premium
Enantioselective Synthesis of All‐Carbon Quaternary Centers Structurally Related to Amaryllidaceae Alkaloids
Author(s) -
Mikušek Jiří,
Jansa Petr,
Jagtap Pratap R.,
Vašíček Tomáš,
Císařová Ivana,
Matoušová Eliška
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802493
Subject(s) - stereocenter , enantioselective synthesis , amaryllidaceae alkaloids , quaternary carbon , stereochemistry , amaryllidaceae , tandem , chemistry , enantiomer , combinatorial chemistry , absolute configuration , alkaloid , organic chemistry , catalysis , biology , materials science , botany , composite material
Enantioselective synthesis of all‐carbon quaternary centers remains a considerable challenge for synthetic organic chemists. Here, we report a two‐step protocol to synthesize such centers including tandem cyclization/Suzuki cross‐coupling followed by halocarbocyclization. During this process, two rings, three new C−C bonds and a stereochemically defined all‐carbon quaternary center are formed. The absolute configuration of this center is controlled by the stereochemistry of the adjacent stereocenter, which derives from an appropriate enantioenriched starting material. Using this method, we synthesized polycyclic compounds structurally similar to Amaryllidaceae alkaloids in high enantiomeric excesses. Because these products resemble naturally occurring compounds, our protocol can be used to synthesize various potentially bioactive compounds.