1H- and 13C-NMR Spectroscopic Studies of Selected Quassinoids

Matthias O. Hamburger; Geoffrey A. Cordell

doi:10.1055/s-2006-962456

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Planta Med 1988; 54(4): 352-355
DOI: 10.1055/s-2006-962456

Papers

¹H- and ¹³C-NMR Spectroscopic Studies of Selected Quassinoids

Matthias O. Hamburger, Geoffrey A. Cordell

Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Il linois 60612, U.S.A.

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1987

Publikationsdatum:
24. Januar 2007 (online)

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Abstract

The ¹³C-NMR spectra of some selected C₂₀ quassinoids have been investigated. Unambiguous assignments were obtained through one-bond and long-range heteronuclear correlation spectroscopy. Some previous assignments have been corrected and ambiguities clarified. The usefulness of one-dimensional, long-range, proton-carbon correlation for the structure elucidation of the highly functionalized picrasan skeleton has been demonstrated. Proton homonuclear spectroscopy (COSY and delayed COSY) was useful for establishing the relative stereochemistry at C-1 and C-12, and several diagnostic, long-range couplings are reported for the first time for the picrasan skeleton.