| Pestalotiopsin a. Enantioselective construction of potential building blocks derived from antipodal cyclobutanol intermediates. | |
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MedLine Citation:
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PMID: 17696474 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1). |
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Authors:
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Leo A Paquette; Gregory D Parker; Takahiro Tei; Shuzhi Dong |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2007-08-15 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 72 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2007 Sep |
Date Detail:
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Created Date: 2007-09-07 Completed Date: 2007-10-16 Revised Date: 2009-04-28 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7125-34 Citation Subset: IM |
Affiliation:
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Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210, USA. paquette.1@osu.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Alcohols
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chemical synthesis*,
chemistry Bicyclo Compounds / chemistry Cyclobutanes / chemical synthesis*, chemistry Lactones / chemistry Sesquiterpenes / chemical synthesis* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Alcohols; 0/Bicyclo Compounds; 0/Cyclobutanes; 0/Lactones; 0/Sesquiterpenes; 0/pestalotiopsin A |
| Comments/Corrections | |
Erratum In:
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J Org Chem. 2009 Feb 20;74(4):1812 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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