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First, Atropo‐Enantioselective Total Synthesis of the Axially Chiral Phenylanthraquinone Natural Products Knipholone and 6′‐ O ‐Methylknipholone
Author(s) -
Bringmann Gerhard,
Menche Dirk
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010504)40:9<1687::aid-anie16870>3.0.co;2-6
Subject(s) - enantioselective synthesis , intramolecular force , lactone , total synthesis , stereochemistry , natural product , axial symmetry , stereoselectivity , chemistry , cleavage (geology) , ring (chemistry) , combinatorial chemistry , organic chemistry , mathematics , materials science , catalysis , geometry , fracture (geology) , composite material
The first stereoselective access to an axially chiral arylanthraquinone , the antimalarial natural product knipholone ( 3 ), was achieved by application of the “lactone concept”. Key steps were the intramolecular coupling of the bromoester 1 , to give the configurationally unstable biaryl lactone 2 , and the enantioselective ring cleavage to form 3 .