Reactions of nepenthone with chromium(II) reagents in neutral aqueous medium

Authors
Micskei, K Gyarmati, J Kovacs, G Makleit, S Simon, C Szabo, Z Marton, J Hosztafi, S Reinke, H Drexler, HJ
Citation
K. Micskei et al., Reactions of nepenthone with chromium(II) reagents in neutral aqueous medium, EUR J ORG C, (1), 1999, pp. 149-153
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
1
Year of publication
1999
Pages
149 - 153
Database
ISI
SICI code
1434-193X(199901):1<149:RONWCR>2.0.ZU;2-Q
Abstract
A synthetic method for the selective transformations of a selected morphine alkaloid in neutral aqueous medium is introduced. Full diastereoselectivit y was achieved by the transformation of nepenthone (1) with [Cr(ida)(H2O)(3 )] into 2a (20R) showing a complementary method as compared to the reaction s with classical reagents to result in 2b (20S). A new unexpected morphine derivative 3 was prepared by a ligand-induced modification of the reaction which involves an unprecedented rearrangement.