Masked o-Benzoquinones in Organic Synthesis
An account of the synthetic utility of masked o-benzoquinones is provided. The inter- and intramolecular Diels−Alder reactions of in situ generated masked o-benzoquinones produced cycloadducts in excellent selectivities. New synthetic methodologies have been developed for the synthesis of highly sub...
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Published in | Accounts of chemical research Vol. 35; no. 10; pp. 856 - 866 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
United States
American Chemical Society
01.10.2002
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Online Access | Get full text |
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Summary: | An account of the synthetic utility of masked o-benzoquinones is provided. The inter- and intramolecular Diels−Alder reactions of in situ generated masked o-benzoquinones produced cycloadducts in excellent selectivities. New synthetic methodologies have been developed for the synthesis of highly substituted ring systems including bicyclo[2.2.2]octenones, oxatricycles, triquinanes, polysubstituted cyclohexanes, and bicyclo[4.2.2]decenones with complete stereocontrol from easily accessible 2-methoxyphenols via the Diels−Alder reaction of masked o-benzoquinones. Other reactions of adducts derived from masked o-benzoquinones are also described. The efficacy of our methodology is demonstrated by several examples of the total synthesis of natural products. |
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Bibliography: | ark:/67375/TPS-KJ0R0W3V-M istex:6B69EE2D2E3FF0F1209ED92E50DAF2EB6C8AE77E ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0001-4842 1520-4898 |
DOI: | 10.1021/ar000194n |