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Regioselective and Atropoisomeric‐Selective Aryl Coupling to Give Naphthyl Isoquinoline Alkaloids: The First Total Synthesis of ()‐Ancistrocladine
Author(s) -
Bringmann Gerhard,
Jansen Johannes R.,
Rink HeinzPeter
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198609131
Subject(s) - isoquinoline , regioselectivity , intramolecular force , chemistry , stereochemistry , biphenyl , aryl , organic chemistry , catalysis , alkyl
The “most unusuall of all the isoquinoline alkaloids,” the title compound 2 , is characterized by a biphenyl system configurationally stable to above 200°C. The key step in the synthesis is intramolecular CC bond formation in the intermediate 1 , in which the two molecular halves are joined by means of lactone formation.