We thank NOF Corporation, Japan, for a generous supply of 1-palmitoyl lysophosphorylcholine. This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan and the Sasakawa Scientific Research Grant from The Japan Science Society.
Total Synthesis of 2-(5,6-Epoxyisoprostane A2)phosphorylcholine and Elucidation of the Relative Configuration of the Isoprostane Moiety†
Article first published online: 28 APR 2005
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 22, pages 3481–3484, May 30, 2005
How to Cite
Acharya, H. P. and Kobayashi, Y. (2005), Total Synthesis of 2-(5,6-Epoxyisoprostane A2)phosphorylcholine and Elucidation of the Relative Configuration of the Isoprostane Moiety. Angew. Chem. Int. Ed., 44: 3481–3484. doi: 10.1002/anie.200500534
- Issue published online: 24 MAY 2005
- Article first published online: 28 APR 2005
- Manuscript Received: 12 FEB 2005
- aldol reaction;
- total synthesis
The two possible diastereomers of 5,6-epoxyisoprostane A2 were synthesized efficiently through aldol condensations of a substituted cyclopentenone and the corresponding epoxyaldehydes (see picture). The relative configurations of the products were assigned by comparing their 1H NMR spectra with literature data. Condensation of the epoxyisoprostane A2 with lysophosphorylcholine (lyso-PC) then furnished the title lipid.