Source:http://linkedlifedata.com/resource/pubmed/id/17061886
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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
43
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| pubmed:dateCreated |
2006-10-25
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| pubmed:abstractText |
The first synthesis of the structurally unique marine natural product antheliolide A (1) has been accomplished by the pathway outlined in Scheme 1. The sequence is stereocontrolled and has led to the synthesis of (+/-)-1, and ent-1 as well as 1. The route contains a number of noteworthy or novel steps including (1) formation of the mixed acetal 7, (2) the diastereoselective bicyclization to form 8 in which stereocenters are correctly established at each carbon of the four-membered ring, (3) the chain extension 8 --> 11, (4) the efficient closure of the nine-membered ring of 12, (5) the mild oxidative cleavage sequence 14 --> 17, and (6) the successful and quick formation of the last three rings of 1 from aldehyde 17 via 18. The synthesis of 1 has also resulted in the clarification of its absolute configuration, which had not been determined previously.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:citationSubset |
IM
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| pubmed:chemical | |
| pubmed:status |
MEDLINE
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| pubmed:month |
Nov
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| pubmed:issn |
0002-7863
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| pubmed:author | |
| pubmed:issnType |
Print
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| pubmed:day |
1
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| pubmed:volume |
128
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
14050-2
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| pubmed:dateRevised |
2008-1-17
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| pubmed:meshHeading | |
| pubmed:year |
2006
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| pubmed:articleTitle |
Total synthesis of antheliolide A.
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| pubmed:affiliation |
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
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| pubmed:publicationType |
Journal Article
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