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Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l -Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

✍ Scribed by Hernández, Andrés S.; Thaler, Adrian; Castells, Josep; Rapoport, Henry


Book ID
120450243
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
408 KB
Volume
61
Category
Article
ISSN
0022-3263

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An enantiospeci!ic route to jasmonoid natural products, (+) -methyl epijasmonate and (-) -methyl cucmbate from L-glutamic acid is reported. The key step is a 5-(3,4) ene cyclization of a fmxtionahzed 14diene as chiron. which sets up three chin11 centres with a high degree of diastereoselectivity.