Synthesen und biologische Eigenschaften von Prostaglandinendoperoxiden, Thromboxanen und Prostacyclinen

New Prostacyclin Analogues

“…(c) represents a catalytic cycle of magnesium hydrogenation via anthracenemagnesium (2) as intermediate. This assumption is supported by the experimental finding that the hydrogenation of (2) [eq. (c)] according to our method is considerably faster than the hydrogenation of elemental magnesium.…”

Synthesis of stable prostacyclin analogues from 2,3-disubstituted bicyclo[3.2.0]heptan-6-ones

“…of the Wittig reagent derived from (methoxymethy1)triphenylphosphonium chloride and potassium t-butoxide in tetrahydrofuran furnished the acyclic vinyl ether (8) (87 yo) after chromatography . The transformation (5) -+ (8) using slightly different reaction conditions has been reported previously by the Upjohn group.9…”

“…The synthesis of 9-deoxy-6,9 a-me thanoepox y-A5-prostaglandin F, (1 4) described here (Scheme 1) is notably shorter than the recently published preparation. Previous work from our laboratories has shown that the ketone (3) can be oxidised regioselectively to the ylactone (5) t in almost quantitative yield by the action of buffered peracetic acid in dichloromethane at -78 "C for 4 days.' The hydroxy-groups in lactone (5) were then protected by formation of their tetrahydropyranyl ethers.…”

“…Previous work from our laboratories has shown that the ketone (3) can be oxidised regioselectively to the ylactone (5) t in almost quantitative yield by the action of buffered peracetic acid in dichloromethane at -78 "C for 4 days.' The hydroxy-groups in lactone (5) were then protected by formation of their tetrahydropyranyl ethers. The use of freshly distilled, dry dihydropyran, with pyridinium toluene-fi-sulphonate as acid catalyst, gave the protected lactone (6) in quantitative yield without recourse to chromatographic purification.…”