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Atropo‐Enantioselective Synthesis of the Natural Bicoumarin (+)‐Isokotanin A via a Configurationally Stable Biaryl Lactone
Author(s) -
Bringmann Gerhard,
Hinrichs Jürgen,
Henschel Petra,
Kraus Jürgen,
Peters Karl,
Peters EvaMaria
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:6<1096::aid-ejoc1096>3.0.co;2-z
Subject(s) - chemistry , enantioselective synthesis , kinetic resolution , lactone , stereochemistry , cleavage (geology) , total synthesis , ring (chemistry) , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
The atropo‐enantioselective total synthesis of the axially chiral bicoumarin (+)‐isokotanin A ( 1 ) is described. Key steps were the formation of a configurationally stable seven‐membered biaryl lactone and its kinetic resolution by atroposelective ring cleavage. The previous assignment of the absolute configuration of (+)‐isokotanin A ( 1 ) (and its synthetic precursors) was confirmed by quantum chemical CD calculations. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)