Method for preparing isoprenoid cyclopropane 1,1-dicarboxylates

Details Method for preparing isoprenoid cyclopropane 1,1-dicarboxylates Method for preparing isoprenoid cyclopropane 1,1-dicarboxylates

1990-08-27

1992-03-10

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

562506, 568 35, 568700, C07C 6974

Patent

active

050951360

ABSTRACT:
A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof including the corresponding monocarboxylate, monocarboxylic acid and alcohol derivatives thereof, all of which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.

REFERENCES:
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patent: 4307244 (1981-12-01), Ficini
patent: 4401601 (1983-08-01), Martel
patent: 4642372 (1987-02-01), Martel
Martel, J. et al., Bull. Soc. Chim. Fr. 1967, 985, DAS 1289046 (1969).
Arlt, D. et al., "Syntheses of Pyrethroid Acid", Angew. Chem. Int. Ed. Engl. 20, No. 9, 703-722 (Sep. 1981).
Campbell, R. V. M. et al., "Synthesis of (.+-.)-Presqualene Alcohol, (.+-.)-Prephytoene Alcohol, and Structurally Related Compounds", J. C. S. Perkin I, 1975, 897-913.
Hendrickson, J. B. et al., J. Am. Chem. Soc. 1974, 95, 2275-2276.
Capson, T. L. et al., "Synthesis of Ammonium Analogues of Carbocationic Intermediates in the Conversion of Presqualene Diphosphate to Squalene", J. Org. Chem. 1988, 53, 5903-5908.
Poulter, C. D. et al., "Squalene Synthetase. Inhibition by Ammonium Analogues of Carbocationic Intermediates in the Conversion of Presqualene Diphosphate to Squalene", J. Am. Chem. Soc. 1989, 111, 3734-3739.
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