Synthesis of Naturally Occurring Helminthic Phosphodiesters and Related Analogues |
| |
| Authors: | Melvin R Euerby William A Gibbons Lynda Z Partridge |
| |
| Institution: | Department of Pharmaceutical Chemistry , School of Pharmacy, University of London , 29-39 Brunswick Square, London , WC1N 1AX , England |
| |
| Abstract: | Abstract Our preliminary findings in the use of 1,3,2-oxazaphospholidin-2-ones (III) as useful synthons in the synthesis of naturally occurring helminthic (worm) phosphodiesters i.e. Opheline(II, R=Me) and serine ethanolamine phosphate (I, R=NH2(CO2H)CHCH2,R′=H)] and of related compounds are reported. The 1,3,2-oxazaphospholidin-2-ones can be synthesised by routes A and B; once formed these can be ring-opened by acid treatment which causes exclusive N-P bond fission yielding the phosphodiesters (I). Guanidinated phosphodiesters (II) have been made by reacting the corresponding phosphodiesters (I,R′=H) with O-methylisourea. |
| |
| Keywords: | |
|
|
