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Phosphorus-containing polyprenoids play an important role in metabolic processes in living organisms (biosynthesis of glicosylaminoglycanes and glycoproteins, terpenes, and geraniol and nerol pyrophosphates) [134]. There are scarce data in the literature on phosphorus-containing isoprenoids with a P3C bond. Synthesis of such compounds is a challenging problem of natural chemistry, that consist of design of new types of phosphorylated 1,5-polyenes and polyterpenes as promising low-molecular bioregulators. Considering the complex structure of ÄÄÄÄÄÄÄÄÄÄÄÄ natural polyisoprenylaldehydes, we made an attempt to develop methods of phosphorylation of such compounds on the basis of their low-molecular analogs. In the present work we showed that a representative of long-chain unsaturated aldehydes, citral I (a mixture of the E and Z isomers), can unidirectionally react with such normal phosphites as trimethyl phosphite in the presence of acetic acid under mild conditions to give a mixture of the E and Z isomers of dimethyl 1-hydroxy-3,7-dimethylocta-2,6-dienylphosphonate (III) in high yield.

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Use of potassium carbonate, sodium sulfide and sodium alkylthiolates results in the reactivity enhancement of phosphorus sulfides (P4Sl0, P4S, and P4S5) and alkyl homologues of Davy's reagent in their reactions with alkyl halides and dialkyl di sulfides.

S-(Diethylamino)dimethylsilyl bis-(diethylamido)dithiophosphate

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