Biomimetic Cycloaddition Approach to Tropolone Natural Products via a Tropolone Ortho-quinone Methide

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 orth...

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Bibliographic Details
Published in:Organic letters 2002-08, Vol.4 (17), p.3009-3011
Main Authors: Adlington, Robert M, Baldwin, Jack E, Mayweg, Alexander V. W, Pritchard, Gareth J
Format: Article
Language:English
Subjects:
Anemia - drug therapy
Erythropoietin - genetics
Gene Expression - drug effects
Indolequinones
Indoles - chemistry
Molecular Mimicry
Quinones - chemistry
Sesquiterpenes - chemistry
Tropolone - analogs & derivatives
Tropolone - chemical synthesis
Tropolone - pharmacology
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol026467r