| Generation and hetero-Diels-Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals. | |
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MedLine Citation:
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PMID: 18633540 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Deprotonation of o-hydroxybenzyl acetate with (i)PrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2pi partners in hetero-Diels-Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6. |
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Authors:
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Christopher D Bray |
Publication Detail:
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Type: Journal Article Date: 2008-05-28 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 6 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2008 Aug |
Date Detail:
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Created Date: 2008-07-17 Completed Date: 2008-10-14 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 2815-9 Citation Subset: IM |
Affiliation:
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School of Biological and Chemical Sciences, The Walter Besant Building, Queen Mary, University of London, London, UK. c.bray@qmul.ac.uk |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Anions
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chemistry Benzene Derivatives / chemical synthesis, chemistry* Furans / chemical synthesis* Indolequinones / chemical synthesis, chemistry* Molecular Structure Protons Spiro Compounds / chemical synthesis* |
| Chemical | |
Reg. No./Substance:
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0/Anions; 0/Benzene Derivatives; 0/Furans; 0/Indolequinones; 0/Protons; 0/Spiro Compounds; 0/spiroketal; 138230-21-4/quinone methide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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