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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
8
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pubmed:dateCreated |
2006-4-7
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pubmed:abstractText |
The synthesis of (-)-stemoamide was achieved in 11 steps from 5-acetoxy-N-crotyl pyrrolidinone. A chiral N-acyl thiazolidinethione was employed in a stereoselective addition to a cyclic N-acyl iminium ion to install the required stereochemistry of carbon C9a. This iminium ion addition product was employed in a stereoselective MgBr2-catalyzed anti-aldol reaction to install the required stereochemistry of carbons C8 and C9. The X-ray crystal analysis of (-)-stemoamide confirmed the structure and the stereochemical outcome of these selective reactions.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Apr
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pubmed:issn |
0022-3263
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
14
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pubmed:volume |
71
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3287-90
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pubmed:meshHeading |
pubmed-meshheading:16599632-Aldehydes,
pubmed-meshheading:16599632-Alkaloids,
pubmed-meshheading:16599632-Azepines,
pubmed-meshheading:16599632-Crystallography, X-Ray,
pubmed-meshheading:16599632-Heterocyclic Compounds, 3-Ring,
pubmed-meshheading:16599632-Lactones,
pubmed-meshheading:16599632-Molecular Structure,
pubmed-meshheading:16599632-Stereoisomerism,
pubmed-meshheading:16599632-Thiazolidines
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pubmed:year |
2006
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pubmed:articleTitle |
Synthesis of (-)-stemoamide using a stereoselective anti-aldol step.
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pubmed:affiliation |
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, USA. horacio-olivo@uiowa.edu
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.
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