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 prosta
The synthesis of nitrogen-containing prostacyclin analogs
β Scribed by G.L. Bundy; J.M. Baldwin
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 372 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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. Am. Chem. Sot. _ 87 (4), 749 (1965) for a thorough study of the decomposition of olefinic asides.
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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.