| pubmed-article:19697910 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:19697910 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:19697910 | lifeskim:mentions | umls-concept:C0439810 | lld:lifeskim |
| pubmed-article:19697910 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:19697910 | lifeskim:mentions | umls-concept:C0763312 | lld:lifeskim |
| pubmed-article:19697910 | pubmed:issue | 18 | lld:pubmed |
| pubmed-article:19697910 | pubmed:dateCreated | 2009-9-11 | lld:pubmed |
| pubmed-article:19697910 | 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. | lld:pubmed |
| pubmed-article:19697910 | pubmed:language | eng | lld:pubmed |
| pubmed-article:19697910 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19697910 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:19697910 | pubmed:month | Sep | lld:pubmed |
| pubmed-article:19697910 | pubmed:issn | 1520-6904 | lld:pubmed |
| pubmed-article:19697910 | pubmed:author | pubmed-author:WiemerDavid... | lld:pubmed |
| pubmed-article:19697910 | pubmed:author | pubmed-author:NeighborsJeff... | lld:pubmed |
| pubmed-article:19697910 | pubmed:author | pubmed-author:TopczewskiJos... | lld:pubmed |
| pubmed-article:19697910 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:19697910 | pubmed:day | 18 | lld:pubmed |
| pubmed-article:19697910 | pubmed:volume | 74 | lld:pubmed |
| pubmed-article:19697910 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:19697910 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:19697910 | pubmed:pagination | 6965-72 | lld:pubmed |
| pubmed-article:19697910 | pubmed:meshHeading | pubmed-meshheading:19697910... | lld:pubmed |
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| pubmed-article:19697910 | pubmed:meshHeading | pubmed-meshheading:19697910... | lld:pubmed |
| pubmed-article:19697910 | pubmed:year | 2009 | lld:pubmed |
| pubmed-article:19697910 | pubmed:articleTitle | Total synthesis of (+)-schweinfurthins B and E. | lld:pubmed |
| pubmed-article:19697910 | pubmed:affiliation | Department of Chemistry University of Iowa, Iowa City, Iowa 52242-1294, USA. | lld:pubmed |
| pubmed-article:19697910 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:19697910 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
