The reaction of C-alkylation of eudesmanolide (–)-α-santonin

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F19%3A10466660" target="_blank" >RIV/00216208:11310/19:10466660 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=zgE1HDuKYL" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=zgE1HDuKYL</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.31489/2019Ch2/14-18" target="_blank" >10.31489/2019Ch2/14-18</a>

Result language
angličtina
Original language name
The reaction of C-alkylation of eudesmanolide (–)-α-santonin
Original language description
This article is concerned with sesquiterpene gamma-lactones of the eudesman structure, which is promising class of natural organic compounds and characterized by a wide spectrum of physiological activity. Stereoselective synthesis of new practically significant 4 alpha(ethyl)-3-keto-trans-eudesm-1(2),5(6)-diene-6,12-olide(C4-α-ethyl-santonin) was carried out at room temperature in argon atmosphere by interaction of eudesmanolide (-)-α-santonin and an organohalide in presence of a strong base: tert-butyl-potassium: dimethylsulfoxide: tert-butyl alcohol. The yield was 50 %. The spatial structure of the synthesized C4-α-ethyl-santonin was established by (1)H NMR-, 2D NMR (COZY, NOESY), mass spectrometry and X-ray analysis. According to the results of X-ray analysis there has been found that the condensed six-membered C4-α-ethyl-santonin cycles are trans-articulated (CH3-10, β-oriented), the ethyl group at C4 has the α-configuration, and the conformation of six-membered eudesmanolide is characterized as distorted chair-chair. Thus, combination of application in the work of modern physico-chemical and spectroscopic research methods allowed characterization of the structure and properties of the compounds obtained.
Czech name
—
Czech description
—

Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)