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Synlett 1991; 1991(9): 663-664
DOI: 10.1055/s-1991-20834
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An Expeditious Synthesis of Pyrophosphate Analogues of Farnesyl Pyrophosphate Using the Phosphonylating Agent Methyl Methylphosphonomorpholidate

A. R. P. M. Valentijn* , G. A. van der Marel, L. H. Cohen, J. H. van Boom
  • *Gorlaeus Laboratory, P.O. Box 9502, NL-2300 RA Leiden, The Netherlands
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Publication Date:
07 March 2002 (online)

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Reaction of methyl lithiomethylphosphonomorpholidate with farnesyl chloride (1-chloro-3,7,11-trimethyl-2,6,10-dodecatriene) followed by demethylation and subsequent coupling with phosphoric acid or methylphosphonic acid gave O-(farnesylmethylphosphono)phosphate (8; farnesylmethylphosphonic phosphoric anhydride) and O-(farnesylmethylphosphono)methylphosphonate (9; farnesylmethylphosphonic methylphosphonic anhydride), respectively. Furthermore, conversion of title compound 2 into tetrabutylammonium methylphosphonomorpholidate (10) followed by coupling with farnesylphosphonic acid gave O-(farnesylphosphono)methylphosphonate (12; farnesylphosphonic methylphosphonic anhydride).