AMINOCYCLANOLS .2. STEREOCHEMICAL STUDIES ON A NEW CIRAMADOL ANALOG BY NMR-SPECTROSCOPY

BURGEMEISTER T., OZARSLAN O., ERTAN M., AKGUN H., WIEGREBE W.

ARCHIV DER PHARMAZIE, vol.327, no.12, pp.785-787, 1994 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 327 Issue: 12
  • Publication Date: 1994
  • Doi Number: 10.1002/ardp.19943271206
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.785-787
  • Middle East Technical University Affiliated: No

Abstract

The absol. configuration of a Ciramadol analogue obtained from (-)-menthone is established by H-1-NMR-, simulated NMR-, COSY-90-, and NOE-measurements. The final compound 2-(alpha-1-pyrrolidino)benzyl-4-isopropyl-1-methyl-cyclohexan-3-one (4b), e.g., has 1R,2S,4S,11S-configuration due to stereoselective Michael-type addition of pyrrolidine to the pertinent benzylidene intermediate 3.