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US 4,520,207 AGranted
Synthesis of thiophene-containing prostaglandin endoperoxide analogs
AssigneeIowa State University Research Foundation, Inc.
InventorRichard C. Larock
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Abstract
New organopalladium reactions involving the addition of thienylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced blood platelet aggregation, and are specific inhibitors of thromboxane synthetase.
Claims6
A method of forming thiophene-containing prostaglandin endoperoxide analogs of the formula:
- ##STR21## wherein n equals a whole integer of from 0 to 7, X is carboxylic acid, or C.sub.1 -C.sub.8 ester, alcohol, ether or amide groups;
- Y is ethylene or cis or trans vinylene;
- A is methylene, ethylene, oxy, imino, or lower alkyl, phenyl or aryl substituted imino;
- D is methylene, ethylene, vinylene, methyleneoxy, alkylidenedioxy, iminooxy, dithio, or azo;
- B is ethylene, cis and trans vinylene, and ethynylene;
- R and R.sub.1 are hydrogen, lower alkyl and lower aryl or (CH.sub.2).sub.Z with Z being 2 to 5, and Q is hydroxy, methoxy, acetoxy or hydrogen, or Q and R.sub.1 are oxa, said method comprising:
- reacting an organomercurial of the formula:
- ##STR22## wherein X and Y are as previously defined, with a bicyclic olefin of the formula:
- ##STR23## wherein A and D are as previously defined, in the presence of a lithium palladium chloride complex to provide a bicyclic alkyl palladium compound of the formula:
- ##STR24## wherein A, D, n and X are as previously defined;
- and displacing the palladium moiety of said alkyl palladium compound with a protected lithium acetylide to provide said thiophene-containing endoperoxide analog.
8 more elements
Dependencies are inferred from the claim text.