The synthesis of solasodine F-homo-analogues
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F19%3A00510300" target="_blank" >RIV/61389030:_____/19:00510300 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/19:73598518
Result on the web
<a href="http://dx.doi.org/10.1039/c9ob01888c" target="_blank" >http://dx.doi.org/10.1039/c9ob01888c</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c9ob01888c" target="_blank" >10.1039/c9ob01888c</a>
Alternative languages
Result language
angličtina
Original language name
The synthesis of solasodine F-homo-analogues
Original language description
Solasodine derivatives continue to be attractive targets for synthetic chemists due to their interesting biological properties. Herein, we report a concise synthesis of solasodine analogues containing the seven-membered F ring from diosgenin. The key intermediate in the synthesis of 26a-homosolane derivatives was 26-cyanopseudodiosgenin. After reduction of the cyano group, the seven-membered ring was closed with MgBr2·Et2O to yield 26a-homosolanes as a mixture of 22R and 22S epimers. The acylation of the obtained mixture led to the diastereomerically pure 22S N-acylated 26a-homosolasodine derivatives. Moreover, we describe one-step protocol for stereoselective synthesis of 22R-cyanofurostane by treatment of diosgenin with TMSCN/BF3·Et2O.
Czech name
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Czech description
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Classification
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
Result continuities
Project
<a href="/en/project/GA19-01383S" target="_blank" >GA19-01383S: Modulation of steroid receptors in human cancer cells by brassinosteroids.</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic & Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
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Volume of the periodical
17
Issue of the periodical within the volume
40
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
9050-9058
UT code for WoS article
000490731400013
EID of the result in the Scopus database
2-s2.0-85073489774