| Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol. | |
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MedLine Citation:
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PMID: 22721256 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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In this study we used sequential catalysis-PPh(3)--catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization--to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol. |
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Authors:
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Yi Chiao Fan; Ohyun Kwon |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2012-06-21 |
Journal Detail:
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Title: Organic letters Volume: 14 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2012 Jul |
Date Detail:
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Created Date: 2012-07-06 Completed Date: 2012-11-07 Revised Date: 2013-04-16 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 3264-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Benzofurans
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chemical synthesis*,
chemistry Catalysis Molecular Structure Palladium / chemistry* Phosphines / chemistry* Phthalic Acids / chemical synthesis*, chemistry Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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P41 GM081282/GM/NIGMS NIH HHS; P41GM081282/GM/NIGMS NIH HHS; R01 GM071779/GM/NIGMS NIH HHS; R01GM071779/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/3-deoxyisoochracinic acid; 0/Benzofurans; 0/Phosphines; 0/Phthalic Acids; 0/isoochracinic acid; 0/isoochracinol; 7440-05-3/Palladium; 7803-51-2/phosphine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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