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SM ISO690:2012 GRINCO, Marina, UNGUR, Nikon. One step synthesis of manoyl oxide derivatives by Horner-Wadsworth-Emmons reaction conditions. In: The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova, 28-30 mai 2014, Chișinău. Chișinău, Republica Moldova: Institutul de Chimie al AȘM, 2014, p. 202. |
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The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova 2014 | ||||||
Conferința "The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova" Chișinău, Moldova, 28-30 mai 2014 | ||||||
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Functionalized derivatives of manoyl oxide are labdane-type diterpenoids isolated from Scheme 1 |
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Cerif XML Export
<?xml version='1.0' encoding='utf-8'?> <CERIF xmlns='urn:xmlns:org:eurocris:cerif-1.5-1' xsi:schemaLocation='urn:xmlns:org:eurocris:cerif-1.5-1 http://www.eurocris.org/Uploads/Web%20pages/CERIF-1.5/CERIF_1.5_1.xsd' xmlns:xsi='http://www.w3.org/2001/XMLSchema-instance' release='1.5' date='2012-10-07' sourceDatabase='Output Profile'> <cfResPubl> <cfResPublId>ibn-ResPubl-106384</cfResPublId> <cfResPublDate>2014</cfResPublDate> <cfStartPage>202</cfStartPage> <cfISBN></cfISBN> <cfURI>https://ibn.idsi.md/ro/vizualizare_articol/106384</cfURI> <cfTitle cfLangCode='EN' cfTrans='o'>One step synthesis of manoyl oxide derivatives by Horner-Wadsworth-Emmons reaction conditions</cfTitle> <cfAbstr cfLangCode='EN' cfTrans='o'><p>Functionalized derivatives of manoyl oxide are labdane-type diterpenoids isolated from<br />natural source and possessing significant biological properties [1, 2].<br />The current report presents the results on the synthesis of some C-15 functionalized<br />derivatives of manoyl- and 13-epi-manoyl oxide (1a) and (2a), obtained from Horner-<br />Wadsworth-Emmons’s (HWE) reaction. As starting material for HWE reaction some<br />bisnorlabdanic keto-derivatives (3a-3c), readily available from either commercial (-)-sclareol<br />(4a) or its diacetate (4b), were used according to the Scheme 1 given below.</p><p>Scheme 1<br />Reagents and conditions: (a) KMnO4, Me2CO, r.t., 5 h, 84%; (b) Ac2O, DCM, 4-DMAP, r.t, 48 h, r.t.<br />90%; (c) TBDMSCl, Py, r.t., 48 h, 25 %; (d) (MeO)2P(O)CH2CO2Me, C6H6, MeONa, reflux, 3 h; (e) 10%<br />KOH, EtOH, reflux, 3 h, 91%.<br />The transformation of ketones (3a-3c) by means of HWE procedure was the key step in the<br />present communication. Reaction yields varied from 72% to 80%, depending on the substrate<br />which was used. The hydroxy ketone (3a) reacted exclusively with the selective formation of the<br />compound (1a) (72%). Both ketones (3b) and (3c) gave a mixture (~2:1) of substances (1a) and<br />(2a). Saponification of esters (1a) and (2a) with an ethanolic solution of potassium hydroxide led<br />to the formation of acids (1b) and (2b), which are the enantiomers of gomeric (5a) and 13-epigomeric<br />(5b) acids, isolated from the medicinal plant Sideritis gomerae [3]. The structure and<br />stereochemistry of the newly synthesized compounds were established on the basis of their<br />spectral data.<br />References:<br />1. Frija, L. M. T.; Frade, R. F. M.; Afonso, C. A. M. Chem. Rev., 2011, 111, 4418–4452.<br />2. Hanson, J. R. Nat. Prod. Rep., 2013, 30, 1346-1356 and privies articles of this series.<br />3. González, A. G.; Fraga, B. M.; Hernández, M. G.; Larruga, F.; Luis, J. Phytochemistry, 1975, 14<br />(12), 2655-2656.</p></cfAbstr> <cfResPubl_Class> <cfClassId>eda2d9e9-34c5-11e1-b86c-0800200c9a66</cfClassId> <cfClassSchemeId>759af938-34ae-11e1-b86c-0800200c9a66</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> </cfResPubl_Class> <cfResPubl_Class> <cfClassId>e601872f-4b7e-4d88-929f-7df027b226c9</cfClassId> <cfClassSchemeId>40e90e2f-446d-460a-98e5-5dce57550c48</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> </cfResPubl_Class> <cfPers_ResPubl> <cfPersId>ibn-person-12130</cfPersId> <cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId> <cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> </cfPers_ResPubl> <cfPers_ResPubl> <cfPersId>ibn-person-672</cfPersId> <cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId> <cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> </cfPers_ResPubl> </cfResPubl> <cfPers> <cfPersId>ibn-Pers-12130</cfPersId> <cfPersName_Pers> <cfPersNameId>ibn-PersName-12130-3</cfPersNameId> <cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId> <cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> <cfFamilyNames>Гринько</cfFamilyNames> <cfFirstNames>Марина</cfFirstNames> </cfPersName_Pers> </cfPers> <cfPers> <cfPersId>ibn-Pers-672</cfPersId> <cfPersName_Pers> <cfPersNameId>ibn-PersName-672-3</cfPersNameId> <cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId> <cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId> <cfStartDate>2014T24:00:00</cfStartDate> <cfFamilyNames>Ungur</cfFamilyNames> <cfFirstNames>Nikon</cfFirstNames> <cfFamilyNames>Унгур</cfFamilyNames> <cfFirstNames>Никон</cfFirstNames> </cfPersName_Pers> </cfPers> </CERIF>