Depentyl analogues of PGA.sub.1

Details Depentyl analogues of PGA.sub.1 Depentyl analogues of PGA.sub.1

1977-04-14

1978-07-11

Gerstl, Robert

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

Organic compounds

Carboxylic acid esters

260514D, C07C17700

Patent

active

041003578

ABSTRACT:
Depentyl analogues of prostaglandins A, E, and F having no C-16 to C-20 carbon atoms. The analogues correspond to the formula ##STR1## wherein: L is methylene, ethylene, or trimethylene;
K is ethylene or cis-vinylene;
M is carbonyl, .alpha.-hydroxymethylene, or .beta.-hydroxymethylene;
N is methylene or methine, provided that N is methine only if P is methine and M is carbonyl;
P is methylene, ethylene, .alpha.-hydroxymethylene or methine, provided that P is methine only if N is methine; and,
R is carboxyl; hydroxymethylene, alkoxycarbonyl, the alkyl portion of said alkoxycarbonyl being a lower alkyl, or a pharmacologically acceptable non-toxic carboxy salt.
The analogues are prepared by first converting a trans-1-iodo-3-alkoxy-1-propene to the corresponding lithio compound. This lithio compound then combines with the hexamethylphosphorous triamide complex of copper(I) pentyne to give an alkenylcopper species. Reacting this alkenylcopper compound with the appropriate 2-substituted-cyclopent-2-enone or 2-substituted-cyclohex-2-enone gives the desired depentyl prostaglandins.

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