Synthesis of Alfaprostol Key Intermediate Ynol via Br/Mg Exchange

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F20%3A39916450" target="_blank" >RIV/00216275:25310/20:39916450 - isvavai.cz</a>
Result on the web
<a href="https://www.tandfonline.com/doi/full/10.1080/00304948.2020.1716623" target="_blank" >https://www.tandfonline.com/doi/full/10.1080/00304948.2020.1716623</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1080/00304948.2020.1716623" target="_blank" >10.1080/00304948.2020.1716623</a>

Result language
angličtina
Original language name
Synthesis of Alfaprostol Key Intermediate Ynol via Br/Mg Exchange
Original language description
We have developed an improved approach to the protected Corey lactone bromoalkyne with a significant increase in yield (35% and 37% in four steps) in comparison with our previous approach (18% over five steps). These compounds serve as starting materials for a novel, simple and reliable synthesis of alfaprostol key intermediate ynol via Br/Mg exchange (72%). The stereoselective effect of BINOL was investigated. We found that influencing stereoselectivity is possible; as to the matter of the S/R isomer ratio, however, a significant reduction in yield of targeted intermediates was observed.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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