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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
18
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pubmed:dateCreated |
2009-9-11
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pubmed:abstractText |
The first total synthesis of (+)-schweinfurthin B, a potent and differentially active cytotoxic agent, has been accomplished. Completion of the synthesis required just 16 steps in the longest linear sequence from commercially available vanillin. Key synthetic transformations included a Shi epoxidation and an efficient cascade cyclization initiated by treatment of the resulting epoxide with BF(3).OEt(2). Furthermore, use of a methyl ether as a stable protecting group for benzylic alcohols dramatically increased the efficiency of the overall sequence. The benzylic ether can be removed from this electron-rich aromatic system through oxidation with DDQ that provided the desired aldehyde intermediate in quantitative yield and shortened the synthetic sequence. Introduction of the A-ring diol in the required cis stereochemistry then became viable through a short sequence highlighted by an aldol condensation with benzaldehyde to introduce an olefin as a latent carbonyl group at the C-3 position. This synthesis established for the first time the absolute stereochemistry of the natural product, and provides access to material on a scale that will advance biological studies. The total synthesis of the closely related compound (+)-schweinfurthin E also is reported.
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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 |
http://linkedlifedata.com/resource/pubmed/chemical/Alkenes,
http://linkedlifedata.com/resource/pubmed/chemical/Antineoplastic Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Benzaldehydes,
http://linkedlifedata.com/resource/pubmed/chemical/Benzene Derivatives,
http://linkedlifedata.com/resource/pubmed/chemical/Benzoquinones,
http://linkedlifedata.com/resource/pubmed/chemical/Boranes,
http://linkedlifedata.com/resource/pubmed/chemical/Epoxy Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Ethers,
http://linkedlifedata.com/resource/pubmed/chemical/Stilbenes,
http://linkedlifedata.com/resource/pubmed/chemical/benzaldehyde,
http://linkedlifedata.com/resource/pubmed/chemical/boron trifluoride,
http://linkedlifedata.com/resource/pubmed/chemical/dichlorodicyanobenzoquinone,
http://linkedlifedata.com/resource/pubmed/chemical/schweinfurthin B
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
1520-6904
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pubmed:author |
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pubmed:issnType |
Electronic
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pubmed:day |
18
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pubmed:volume |
74
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
6965-72
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pubmed:meshHeading |
pubmed-meshheading:19697910-Alkenes,
pubmed-meshheading:19697910-Antineoplastic Agents,
pubmed-meshheading:19697910-Benzaldehydes,
pubmed-meshheading:19697910-Benzene Derivatives,
pubmed-meshheading:19697910-Benzoquinones,
pubmed-meshheading:19697910-Boranes,
pubmed-meshheading:19697910-Cyclization,
pubmed-meshheading:19697910-Epoxy Compounds,
pubmed-meshheading:19697910-Ethers,
pubmed-meshheading:19697910-Models, Chemical,
pubmed-meshheading:19697910-Oxidation-Reduction,
pubmed-meshheading:19697910-Stereoisomerism,
pubmed-meshheading:19697910-Stilbenes
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pubmed:year |
2009
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pubmed:articleTitle |
Total synthesis of (+)-schweinfurthins B and E.
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pubmed:affiliation |
Department of Chemistry University of Iowa, Iowa City, Iowa 52242-1294, USA.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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