Structural assignments for the various synthetic intermediates were confirmed by infrared, proton magnetic resonance and mass spectroscopy on chromatographically homogeneous samples. This cycloaddition probably involves the intermediacy of a triazoline rather than a nitrene. See A.L. Logothetis, J
Synthesis of analogs of prostacyclin containing a thiazone ring
β Scribed by Robert H. Bradbury; Keith A.M Walker
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 313 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
Thiazole analogs of prostacyclln were prepared from the cyclopentene (g), itself. obtained z a novel opening of 3,4-epoxycyclopentene with the llthloallylthloether (4).
Widespread interest ln the synthesis and biological properties of prostacyclin (PGQ,
(1))3 has followed th; discovery that prostacyclln both inhlblts platelet aggregatlon and induces vasodllatlon. However, therapeutic use of prostacyclln 1s precluded by its rapid hydrolysis to 6-oxo-PGFIo, 5 and consequently a wide range of stable analogs of 3 6 prostacyclln has been prepared. '
Of these the only reported "heteroaromatlc"
' Chem. Lett., TW4, 1371.
π SIMILAR VOLUMES
Starting from Y-lactone intermediates, a novel method for the synthesis of the 5,6-dihydro-4H-cyclopenta[blfuran system has been developed which was utilized to prepare furanoprostacyclin derivatives. Because of the inherent instability of prostacyclin towards hydrolytic conditions 2 and its rapid d
The new aromatic prostacyclin analog 3a and 3b were -synthesized from the allylic alcohol 5 in high regio-and stereoselectivity. Prostacyclin (PGI2, \_ 1) possesses the remarkable biological property of inhibiting the fatal effects caused by thromboxane A2. ' There is, however, an obstacle to the u
The synthesis of a novel prostacyclin analog I has been achieved, incorporating as a key strategic feature a regio-controlled epoxide ring opening (as predicted by MM2 calculations) of a readily available prostaglandin synthon.