| pubmed-article:19688787 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:19688787 | lifeskim:mentions | umls-concept:C0010546 | lld:lifeskim |
| pubmed-article:19688787 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:19688787 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:19688787 | lifeskim:mentions | umls-concept:C0243072 | lld:lifeskim |
| pubmed-article:19688787 | pubmed:issue | 10 | lld:pubmed |
| pubmed-article:19688787 | pubmed:dateCreated | 2009-10-6 | lld:pubmed |
| pubmed-article:19688787 | pubmed:abstractText | Diastereocontrolled Lewis acid-catalyzed preparation of enantiopure carbacepham derivatives have been developed starting from 2-azetidinone-tethered enals. The BF3.Et2O-promoted reaction of alkenylaldehydes 1 and 16 is effective as carbocyclization protocol to afford 4-substituted 5-hydroxycarbacephams or 3-substituted 4,5-dihydroxycarbacephams, respectively, by a type I carbonyl-ene reaction, while the BF3.Et2O or SnCl4-mediated type II carbonyl-ene cyclization of alkenylaldehydes 2 furnishes 3-methylene 5-hydroxycarbacephams along with the corresponding 3-halo 5-hydroxycarbacepham. The stereochemical outcome of these carbonyl-ene cyclizations leading to carbacepham derivatives can be explained in terms of six-membered, cyclic chair-like transition-state models. The formation of halocarbacepham derivatives is proposed to proceed by a stepwise mechanism. | lld:pubmed |
| pubmed-article:19688787 | pubmed:language | eng | lld:pubmed |
| pubmed-article:19688787 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19688787 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:19688787 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19688787 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19688787 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19688787 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19688787 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:19688787 | pubmed:month | Oct | lld:pubmed |
| pubmed-article:19688787 | pubmed:issn | 1861-471X | lld:pubmed |
| pubmed-article:19688787 | pubmed:author | pubmed-author:AlcaideBenito... | lld:pubmed |
| pubmed-article:19688787 | pubmed:author | pubmed-author:AlmendrosPedr... | lld:pubmed |
| pubmed-article:19688787 | pubmed:author | pubmed-author:PardoCarmenC | lld:pubmed |
| pubmed-article:19688787 | pubmed:author | pubmed-author:Rodríguez-Ran... | lld:pubmed |
| pubmed-article:19688787 | pubmed:author | pubmed-author:Rodríguez-Vic... | lld:pubmed |
| pubmed-article:19688787 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:19688787 | pubmed:day | 5 | lld:pubmed |
| pubmed-article:19688787 | pubmed:volume | 4 | lld:pubmed |
| pubmed-article:19688787 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:19688787 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:19688787 | pubmed:pagination | 1604-11 | lld:pubmed |
| pubmed-article:19688787 | pubmed:meshHeading | pubmed-meshheading:19688787... | lld:pubmed |
| pubmed-article:19688787 | pubmed:meshHeading | pubmed-meshheading:19688787... | lld:pubmed |
| pubmed-article:19688787 | pubmed:meshHeading | pubmed-meshheading:19688787... | lld:pubmed |
| pubmed-article:19688787 | pubmed:meshHeading | pubmed-meshheading:19688787... | lld:pubmed |
| pubmed-article:19688787 | pubmed:meshHeading | pubmed-meshheading:19688787... | lld:pubmed |
| pubmed-article:19688787 | pubmed:year | 2009 | lld:pubmed |
| pubmed-article:19688787 | pubmed:articleTitle | Lewis acid-assisted ene cyclization of 2-azetidinone-tethered enals: synthesis of enantiopure carbacepham derivatives. | lld:pubmed |
| pubmed-article:19688787 | pubmed:affiliation | Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, E-28040 Madrid, Spain. alcaideb@quim.ucm.es | lld:pubmed |
| pubmed-article:19688787 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:19688787 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
