SYNTHESIS OF BENZOFURANOFURAN DERIVATIVES: MODEL OF NATURAL PRODUCTS

Several benzofuranofuran derivatives were synthesized employing intramolecular cycloaddition reactions of ketenes with alkenes. (Alkenyloxy)ketenes, prepared from the tosylate by treatment with triethylamine, easily undergo intramolecular [2 + 2] cycloaddition to give tricyclic benzocyclobutafuranon...

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Bibliographic Details
Published inSynthetic communications Vol. 31; no. 1; pp. 151 - 154
Main Authors Donate, Paulo Marcos, da Silva, Rosangela, da Silva, Gil Valdo José, Alemán, Carlos
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.01.2001
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COUMARIN
2 CYCLO-ADDITIONS
MICROMELUM-MINUTUM
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Summary:Several benzofuranofuran derivatives were synthesized employing intramolecular cycloaddition reactions of ketenes with alkenes. (Alkenyloxy)ketenes, prepared from the tosylate by treatment with triethylamine, easily undergo intramolecular [2 + 2] cycloaddition to give tricyclic benzocyclobutafuranones. Baeyer-Villiger oxidation of the cycloadducts gives benzofurano-furanones, which are closely related to natural products with anticoagulant and antimalarial properties.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-100000191