1H and13C NMR spectra of biologically active compounds. III. Diastereomers of (�)-7-thia- and 13-thia-16-aryloxy analogs of 11-deoxyprostaglandins of the E1 series

Abstract

The structure has been established and stereochemical assignments have been made of two complete sets of diastereomers of the 7-thia and 13-thia analogs of 11-deoxy-prostaglandins of the E1 series by the13C NMR method. It is proposed to determine the diastereomeric effects of the13C NMR chemical shifts, which are differential parameters bearing information on the stereochemistry of the molecules. Diagnostic diastereomeric effects have been found for assigning stereoisomers with respect to the C-15-hydroxy group and also with respect to the C-8 and C-12 chiral centers of the cyclopentane ring.