Process for preparing optically active 6-t-butyoxy-3,5-dihydroxy

Details Process for preparing optically active 6-t-butyoxy-3,5-dihydroxy Process for preparing optically active 6-t-butyoxy-3,5-dihydroxy

1990-02-27

1991-02-19

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

C07C 6966

Patent

active

049946021

ABSTRACT:
A process for preparing an optically active 6-t-butoxy-3,5-dihydroxyhexanoic ester represented by formula: ##STR1## wherein t-Bu represents a t-butyl group; and R.sup.4 represents a lower alkyl group, which is useful as a precursor of a lactone moiety of campactin, mevinolin or analogues thereof is disclosed, comprising asymmetrically hydrogenating a 4-t-butoxyacetoacetic ester in the presence of a ruthenium-optically active phosphine complex to obtain an optically active 4-t-butyoxy-3-hydroxybutanoic ester, reacting the ester with a lithium enolate of an acetic ester to obtain an optically active 6-t-butyoxy-5-hydroxy-3-oxohexanoic ester, and asymmetrically hydrogenating the resulting ester in the presence of a ruthenium-optically active phosphine complex as a catalyst. The desired product can be obtained in good yield at high stereoselectivity.

REFERENCES:
CA 91(15): 123310n, 1979.
CA 93(25): 238692x, 1980.
CA 108(7): 55601a, 1988.

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