Articolul precedent |
Articolul urmator |
729 0 |
SM ISO690:2012 GÎRBU, Vladilena, GRINCO, Marina, UNGUR, Nikon. Synthesis from (-)-sclareol of some spongiane diterpenoids functionalized in the cycle C. 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. 201. |
EXPORT metadate: Google Scholar Crossref CERIF DataCite Dublin Core |
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 | ||||||
|
||||||
Pag. 201-201 | ||||||
|
||||||
Descarcă PDF | ||||||
Rezumat | ||||||
Spongiane diterpenoids are bioactive natural products isolated exclusively from sponges Scheme 1. Reagents and conditions: (a) mCPBA, CH2Cl2, r.t., over night, 65%%; (b) (iPrO)3Al, PhMe, reflux, |
||||||
|
DataCite XML Export
<?xml version='1.0' encoding='utf-8'?> <resource xmlns:xsi='http://www.w3.org/2001/XMLSchema-instance' xmlns='http://datacite.org/schema/kernel-3' xsi:schemaLocation='http://datacite.org/schema/kernel-3 http://schema.datacite.org/meta/kernel-3/metadata.xsd'> <creators> <creator> <creatorName>Gîrbu, V.M.</creatorName> <affiliation>Institutul de Chimie al AŞM, Moldova, Republica</affiliation> </creator> <creator> <creatorName>Grinco, M.C.</creatorName> <affiliation>Institutul de Chimie al AŞM, Moldova, Republica</affiliation> </creator> <creator> <creatorName>Ungur, N.D.</creatorName> <affiliation>Institutul de Chimie al AŞM, Moldova, Republica</affiliation> </creator> </creators> <titles> <title xml:lang='en'>Synthesis from (-)-sclareol of some spongiane diterpenoids functionalized in the cycle C</title> </titles> <publisher>Instrumentul Bibliometric National</publisher> <publicationYear>2014</publicationYear> <relatedIdentifier relatedIdentifierType='ISBN' relationType='IsPartOf'></relatedIdentifier> <dates> <date dateType='Issued'>2014</date> </dates> <resourceType resourceTypeGeneral='Text'>Conference Paper</resourceType> <descriptions> <description xml:lang='en' descriptionType='Abstract'><p>Spongiane diterpenoids are bioactive natural products isolated exclusively from sponges<br />and marine shell-less mollusks (nudibranchs). They are believed to be spongian-derived<br />metabolites from the sponges which are sequestered by soft corals, hydroids and other sessile<br />marine invertebrates and used as food resources.<br />Most of these compounds play a key role as eco-physiological mediators and are of<br />interest for potential applications as therapeutic agents[1, 2].<br />Synthesis of spongia-13(14)-en-12,15-dione (1) was accomplished starting from (-)-<br />sclareol (2), according to the Scheme 1 given below.</p><p>Scheme 1. Reagents and conditions: (a) mCPBA, CH2Cl2, r.t., over night, 65%%; (b) (iPrO)3Al, PhMe, reflux,<br />18 h, 52%; (c) H2SO4-Dioxane, 90oC, 4 h, 37%; (d) Na2CrO4, AcOH, Ac2O, C6H6, 80oC, 24 h, 82%.<br />Firstly, starting material (2) was transformed into methyl ent-isocopalate (3) in four steps.<br />Then, the last was involved in a short synthetic sequence of epoxidation with m-CPBA and<br />aluminium isopropoxide rearrangement [3] to yield the allylic alcohol (5) in 52% overall yield,<br />which was treated with H2SO4 in dioxan to give a -lactone (6). Sodium chromate oxidation of<br />compound (6) led to the formation of spongiane ,-unsaturated keto-lactone (1), functionalized<br />in C-12 position.<br />References:<br />1. Keyzers, R. A.; Northcote, P. T.; Davies-Coleman, M. T. Nat. Prod. Rep., 2006, 23, 321–334.<br />2. González, M. A. Curr. Bioac. Comp., 2007, 3, 1-36.<br />3. Mischne, M. P.; Sierra, M.; Riiveda, E. A. J. Org. Chem., 1984, 49, 2035-2037.</p></description> </descriptions> <formats> <format>application/pdf</format> </formats> </resource>