Optically active bicyclo[3.3.0]octane and processes for the prep

Details Optically active bicyclo[3.3.0]octane and processes for the prep Optically active bicyclo[3.3.0]octane and processes for the prep

1989-01-04

1989-10-03

Shaver, Paul F.

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

Organic compounds

Silicon containing

549214, C07F 708

Patent

active

048718696

ABSTRACT:
New intermediate, an optically active (1R,5S,6S,7R)-6-tert-butyldiphenylsilyloxmethyl-7-hydroxy-bicyclo[3.3.0]oc tan-3-one (I) having high optical purity which is useful for the synthesis of an optically active carbacyclin and an optically active pentalenolactone E methyl ester. The compound (I) is also an intermediate compound serving for the purpose of improving the optical purity of (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane. The compound (I) is prepared by reacting (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane with tert-butylchlorodiphenylsilane in the presence of a base and removing the ethylenedioxy and tetrahydropyranyl groups of the resultant compound under an acid condition.

REFERENCES:
patent: 4359581 (1982-11-01), Skuballa et al.
patent: 4554363 (1985-11-01), Vorbrueggen
patent: 4644068 (1987-02-01), Shibasaki et al.
patent: 4681951 (1987-07-01), Shibasaki et al.
patent: 4762936 (1988-08-01), Shibasaki et al.

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