Abstract
[reaction: see text] A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anemia / drug therapy
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Erythropoietin / genetics
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Gene Expression / drug effects
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Indolequinones*
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Indoles / chemistry
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Molecular Mimicry
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Monocyclic Sesquiterpenes
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Quinones / chemistry
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Sesquiterpenes / chemistry
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Tropolone / analogs & derivatives*
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Tropolone / chemical synthesis
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Tropolone / pharmacology
Substances
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Indolequinones
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Indoles
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Monocyclic Sesquiterpenes
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Quinones
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Sesquiterpenes
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Erythropoietin
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quinone methide
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humulene
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Tropolone