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Polycyclische Aromatische Alkaloide, V. Synthese von 2‐Bromleptoclinidinon
Author(s) -
Bracher Franz
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900135
Subject(s) - chemistry , amination , pyridine , acetic acid , alkaloid , amine gas treating , ring (chemistry) , reductive amination , organic chemistry , stereochemistry , catalysis
Polycyclic Aromatic Alkaloids, V. – Synthesis of 2‐Bromoleptoclinidinone 4‐Bromo‐2‐nitroacetophenone ( 6 ) is selectively reduced to the amine 7 by Fe in aqueous acetic acid. Oxidative amination of quinolinequinone 8 with 7 gives 9 . Acid‐catalyzed cyclization of 9 , followed by anellation of a pyridine ring, gives the cytotoxic pentacyclic alkaloid 2‐bromoleptoclinidinone ( 3 ).
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