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Investigation of a Domino Heck Reaction for the Rapid Synthesis of Bicyclic Natural Products
Author(s) -
Trost Barry M.,
O'Boyle Brendan M.,
Hund Daniel
Publication year - 2010
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.201001689
Subject(s) - domino , heck reaction , natural product , cascade reaction , chemistry , tandem , combinatorial chemistry , organic chemistry , palladium , catalysis , materials science , composite material
Unexpected Heck : During efforts toward the synthesis of FR900482, an unexpected domino Heck product was isolated (see scheme). Although this pathway was ultimately not productive for the aforementioned natural product synthesis, efforts were made to extend the methodology to the synthesis of amurensinine. To our knowledge this domino reaction was the first such tandem Heck‐alkylation pathway in the presence of a geometrically favorable β‐hydrogen elimination.