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Palladium‐Catalyzed DYKAT of Butadiene Monoepoxide: Enantioselective Total Synthesis of (+)‐DMDP, (−)‐Bulgecinine, and (+)‐Broussonetine G
Author(s) -
Trost Barry M.,
Horne Daniel B.,
Woltering Michael J.
Publication year - 2006
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.200600202
Subject(s) - enantioselective synthesis , synthon , chemistry , palladium , total synthesis , tsuji–trost reaction , catalysis , absolute configuration , stereoselectivity , stereochemistry , alkylation , amine gas treating , combinatorial chemistry , organic chemistry
Palladium catalyzed asymmetric allylic alkylation reaction of an amine with two equivalents of butadiene monoxide allows for the expedient synthesis of trans ‐ and cis ‐2,5‐dihydropyrroles. The versatility of these chiral synthons towards the synthesis of a wide variety of iminosugar natural products was demonstrated with the short and high yielding asymmetric syntheses of (+)‐DMDP, and (−)‐bulgecinine. In addition, the first total synthesis of (+)‐broussonetine G, a potent glycosidase inhibitor, is described along with the assignment of its relative and absolute stereochemical configuration.