Carbon-13 Nuclear Magnetic Resonance Spectra of Prostaglandins and Some Prostaglandin Analogs
- 1 May 1973
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 70 (5), 1579-1584
- https://doi.org/10.1073/pnas.70.5.1579
Abstract
High-resolution pulsed Fourier-transform nuclear magnetic resonance spectroscopy at 22.63 MHz was used to observe the proton-decoupled natural-abundance (13)C nuclear magnetic resonance spectra of CDCl(3) solutions of the methyl esters of prostaglandins F(1alpha), 15-epi-F(1alpha), F(2alpha), F(2beta), E(2), A(2), 13-dehydro-F(2alpha), 13-dehydro-F(3alpha), two intermediates on the synthetic pathway to 13-dehydro-PGF(3alpha), and of 7-oxa-PGF(1alpha). All resonances were assigned by chemical shift comparisons and single-frequency offresonance proton decoupling. With two exceptions, all the lines of the spectra are well-resolved single-carbon resonances. Those due to the cyclopentane and vinyl carbons are most sensitive to structural changes. Some of these effects can be rationalized in terms of the preferred conformations of the molecules.Keywords
This publication has 5 references indexed in Scilit:
- Synthesis and biological effects of 13-dehydro derivatives of natural prostaglandin F2.alpha. and E2 and their 15-epienantiomersJournal of Medicinal Chemistry, 1973
- Molecular conformation of prostaglandin A1Prostaglandins, 1973
- Synthesis of (+)- and (-)-7-oxaprostaglandin F1.alpha. and their 15-epimersJournal of the American Chemical Society, 1971
- SYNTHESIS AND BIOLOGICAL ACTIVITY OF PROSTAGLANDINS AND PROSTAGLANDIN ANTAGONISTSAnnals of the New York Academy of Sciences, 1971
- Total synthesis of prostaglandins. Synthesis of the pure dl-E1, -F(sub 1.alpha.), -F(sub 1.beta.), -A1, and -B1 hormonesJournal of the American Chemical Society, 1968