Prostaglandin intermediates and optically active isomers thereof

Details Prostaglandin intermediates and optically active isomers thereof Prostaglandin intermediates and optically active isomers thereof

1975-03-24

1976-09-14

Killos, Paul J.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260471A, 260473A, 260521R, C07C 6514

Patent

active

039807002

ABSTRACT:
The condensation of dimethyl 3-oxoundecane-1,11-dioate with styrylglyoxal affords 14-phenyl-9,12-dioxo-11-hydroxytetradec-13-enoic acid, which is cyclized to afford 3-hydroxy-5-oxo-2-styrylcyclopent-1-eneheptanoic acid. Hydroxylation of the styryl double bond affords the corresponding 2-(.alpha.,.beta.-dihydroxyphenethyl) derivative. Resolution of the racemic 2-styryl-3-hydroxy compounds with either (-) or (+)-O-methylmandelyl chloride yields the optically active isomers which are separated chromatographically. The instant compounds are useful as anti-microbial, anti-fungal and hypotensive agents, as prostaglandin (PGE.sub.2) antagonists and also as intermediates to prostanoic acid derivatives and their optically active isomers which exhibit anti-microbial, pepsin-inhibitory, hypotensive and smooth muscle-contracting properties.

REFERENCES:
miyano, M. et al., Tetrahedron Letters No. 20, pp. 1615-1618, 1969.

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