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Palladium‐Catalyzed Additions of Alkenyl Epoxides to Pronucleophiles: A Synthesis of the Macrolactam Aglycone of Fluviricin B1
Author(s) -
Trost Barry M.,
Ceschi Marco A.,
König Burkhard
Publication year - 1997
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.199714861
Subject(s) - aglycone , stereocenter , catalysis , chemistry , enantioselective synthesis , chirality (physics) , palladium , stereochemistry , alkyl , organic chemistry , physics , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark , glycoside
Chirality transfer takes place during the Pd‐catalyzed reaction of pronucleophiles with vinyl epoxides bearing and alkyl group at the vinyl terminus. The reaction is ideal to establish remote stereogenic centers. A synthesis of fluviricin B1 aglycone 3 from 1 and 2 illustrates the application of this new strategy for macrolactamization.