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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
3
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pubmed:dateCreated |
2009-1-21
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pubmed:abstractText |
A nontraditional approach to the enantiocontrolled construction of quaternary center-bearing heteroatom-bridged bicyclo[3.3.1]nonanes (homotropanes) is reported that is based on organometallic enantiomeric scaffolding. This strategy takes advantage of the unique reactivity profiles of TpMo(CO)(2)(5-oxo-eta(3)-pyranyl) and TpMo(CO)(2)(5-oxo-eta(3)-pyridinyl) scaffolds, and features a molybdenum-mediated semipinacol/1,5-"Michael-like" reaction sequence to establish the quaternary center and synthesize the bridged bicyclic structure. An asymmetric total synthesis of (-)-adaline highlights this methodology.
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pubmed:grant |
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pubmed:commentsCorrections |
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-11076602,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-11101451,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-11414856,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-11741410,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-12123353,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-12153279,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-12617646,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-14724294,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-15232003,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-15369354,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-16089451,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-16402833,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-17284010,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-18171075,
http://linkedlifedata.com/resource/pubmed/commentcorrection/19123794-18479131
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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 |
Jan
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pubmed:issn |
1520-5126
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:day |
28
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pubmed:volume |
131
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
876-7
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pubmed:dateRevised |
2011-9-26
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pubmed:meshHeading |
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pubmed:year |
2009
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pubmed:articleTitle |
Organometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.
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pubmed:affiliation |
Sanford S. Atwood Chemistry Center, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
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pubmed:publicationType |
Journal Article,
Research Support, N.I.H., Extramural
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