Zur Kenntnis der <i>o</i>‐Chinone, XVII. Darstellung und Additionsverhalten von <i>o</i>‐Chinonen des 6.7‐Benzotropolons

Horner, L.; Göwecke, Siegfried; Dürckheimer, Walter

doi:10.1002/cber.19610940517

Cited by 18 publications

References 9 publications

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TheThiele‐Winter Acetoxylation of Quinones

McOmie

Blatchly²

2011

Organic Reactions

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In 1898, Johannes Thiele described the reaction of p‐benzoquinone with acetic acid in the presence of a small quantity of sulfuric acid to give 1,2,4‐triacetoxybenzene in 80% yield. Later Thiele and Winter described further experiments that showed both 1,2‐ and 1,4‐naphthoquinone gave 1,2,4‐triacetoxynaphthalene and that the same product was obtained when sulfuric acid was replaced by zinc chloride. Thiele‐Winter acetoxylation can be defined as the acid‐catalyzed reactions of quinones with acetic acid to give triacetoxy aromatic compounds. This reaction has been carried out on a large number of quinones and to this point there has been no review. Very little work has been done on the reaction of quinones with anhydrides other than acetic anhydride. Results of these studies are summarized. Reactions with other anhydrides are discussed.

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TheThiele‐Winter Acetoxylation of Quinones

McOmie

Blatchly²

2011

Organic Reactions

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Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

2014

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Dibefurin is a C i -symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.

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Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

2014

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Dibefurin is a Ci -symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.

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Zur Kenntnis der o‐Chinone, XVII. Darstellung und Additionsverhalten von o‐Chinonen des 6.7‐Benzotropolons

Cited by 18 publications

References 9 publications

TheThiele‐Winter Acetoxylation of Quinones

TheThiele‐Winter Acetoxylation of Quinones

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin

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