Synthesis of pyrophosphonic acid analogues of farnesyl pyrophosphate

The synthesis of four new analogues ( i.e. 3–6) of farnesyl pyrophosphate (FPP), which may function as inhibitor of squalene synthase, is described. Compounds 3 and 4 were readily accessible by reaction of farnesal with diethyl phosphite or dimethyl lithiomethylphosphonate, respectively, followed by...

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Bibliographic Details
Published in:Tetrahedron 1995-02, Vol.51 (7), p.2099-2108
Main Authors: Valentijn, A.R.P.M., van den Berg, O., van der Marel, G.A., Cohen, L.H., van Boom, J.H.
Format: Article
Language:English
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Summary:The synthesis of four new analogues ( i.e. 3–6) of farnesyl pyrophosphate (FPP), which may function as inhibitor of squalene synthase, is described. Compounds 3 and 4 were readily accessible by reaction of farnesal with diethyl phosphite or dimethyl lithiomethylphosphonate, respectively, followed by condensation of the resulting alcohols with diethyl phosphonomethyl triflate. The preparation of 5 and 6 was accomplished by alkylation of bis(diethyl phosphonomethyl) ether or tetraethyl methylenebisphosphonate, respectively, with farnesyl bromide. The synthesis of four new potential inhibitors of squalene synthase is described.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(94)01083-C