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

LIBRIS-ID:oai:DiVA.org:kth-317897
https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-317897URI
https://doi.org/10.1002/(sici)1099-0690(199901)1999:1<149::aid-ejoc149>3.0.co;2-zDOI

QC 20220915
A synthetic method for the selective transformations of a selected morphine alkaloid in neutral aqueous medium is introduced. Full diastereoselectivity was achieved by the transformation of nepenthone (1) with [Cr(ida)(H2O)3] into 2a (20R) showing a complementary method as compared to the reactions 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.

Gyarmati, J. (author)
Kovács, G. (author)
Makleit, S. (author)
Simon, C. (author)
Szabo, Zoltan,Associate professorICN-Alkaloida Hungary Company Ltd., H-4440 Tiszavasvári, Hungary(Swepub:kth)u1ffpq7p (author)
Marton, J. (author)
Hosztafi, S. (author)
Reinke, H. (author)
Drexler, H. -J (author)
ICN-Alkaloida Hungary Company Ltd., H-4440 Tiszavasvári, Hungary (creator_code:org_t)

By the author/editor: Micskei, K.; Gyarmati, J.; Kovács, G.; Makleit, S.; Simon, C.; Szabo, Zoltan, A ...; show more...; Marton, J.; Hosztafi, S.; Reinke, H.; Drexler, H. -J; show less...

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