Process for preparing 3-alkenylidene-1,1-bisphosphonates

Details Process for preparing 3-alkenylidene-1,1-bisphosphonates Process for preparing 3-alkenylidene-1,1-bisphosphonates

1991-05-13

1992-04-07

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus esters

C07F 940

Patent

active

051030365

ABSTRACT:
A process is provided for preparing a 3-alkenylidene-1,1-bisphosphonate which is an intermediate for preparing an inhibitor of the enzyme squalene synthetase which is useful as an inhibitor of cholesterol biosynthesis, or which bisphosphonate itself is useful as an inhibitor of cholesterol biosynthesis. The process involves the palladium catalyzed coupling of an allylic ester with a tetraester of a methylenebisphosphonate to form a 3-alkenylidene-1,1-bisphosphonate containing an alkene moiety located .gamma., .delta. to the phosphonates.

REFERENCES:
Thompson, W., et al., Tetrahedron Letters, 1990, 31, 6819-6822.
Marshall, J., et al., J. Org. Chem., 1987, 52, 2378-2388.
Trost, B., Angew. Chem. Int. Ed. Eng., 1989, 28, 1173-1192.
Trost, B., et al., J. Am. Chem. Soc., 1979, 101, 1595-1597.

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