Source:http://linkedlifedata.com/resource/pubmed/id/15357589
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
19
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| pubmed:dateCreated |
2004-9-10
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| pubmed:abstractText |
The double ring-closing metathesis reaction of N-alkynyl-N-(1,omega)-alkadienyl acrylamides 1 using first- or second-generation Grubbs' catalyst afforded, in a highly selectively manner, the fused bicyclic quinolizidine alkaloid derivatives and their analogues bearing a 1,3-diene moiety, which may further undergo a Diels-Alder reaction with a dienophile to afford N-containing polycyclic compounds. The excellent selectivity of fused/dumbbell-mode cyclization has been realized by the higher reactivity of the electron-rich C=C bond or carbon-carbon triple bond combined with the lower reactivity of the electron-deficient C=C bond toward metallocarbenes and the thermodynamically more stable nature of fused bicyclic compounds 3 vs dumbbell-type bicyclic compounds 4.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:status |
PubMed-not-MEDLINE
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| pubmed:month |
Sep
|
| pubmed:issn |
0022-3263
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
17
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| pubmed:volume |
69
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| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
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| pubmed:pagination |
6305-9
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| pubmed:year |
2004
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| pubmed:articleTitle |
Highly selective synthesis of bicyclic quinolizidine alkaloids and their analogues via double RCM reaction of N-alkynyl-N-(1,omega)-alkadienyl acrylamides.
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| pubmed:affiliation |
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China. masm@mail.sioc.ac.cn
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| pubmed:publicationType |
Journal Article
|