Abstract
Aldosterone exists in solution predominantly as an equilibrating mixture of the 20-oxo-11,18-hemiacetal (2) and the 11,18-epoxy-18,20-hemiacetal (1), resulting in distinct but superimposed n.m.r. spectra. Full assignments of the 1H and 13C spectra have been achieved by carrying out a 13C–13C connectivity experiment (INADEQUATE) to identify the set of 13C signals for each of the two forms, followed by the use of 1H–13C heteronuclear shift-correlated spectroscopy, aided by a phase-sensitive double quantum filtered COSY and 2D J-resolved spectra (1H), with a few selective nuclear Overhauser difference measurements. This permitted assignments of all the 1H and 13C chemical shifts and almost all of the two- and three-bond interproton coupling constants for each tautomer.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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