SYNTHESIS OF A NOVEL NON-BENZENOID QUINONE, 3,10-DIHYDRO-2,4-DIMETHYL-7,13-METHANOCYCLOHEPTA[11]-AN NULENE-3,10-DIONE, FROM 8H-7,9-BIS(METHOXYCARBONYL)-5,11-METHANO[11]ANNULENO[c]FURAN-8-ONE

8H-7,9-Bis(methoxycarbonyl)-5,11-methano[11]anuleno[c]furan-8-one (3) undergoes [4+3] cycloaddition with an oxyallyl species generated from 2,4-dibromo-3-pentanone in the presence of KI and copper, followed by dehydration in fluorosulfuric acid to give cyclohepta[11]annulenedione diester 9. After hy...

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Published inHeterocycles Vol. 86; no. 2; pp. 1541 - 1547
Main Authors Kuroda, Shigeyasu, Matsumoto, Naoko, Zhang, Yanmei, Miyatake, Ryuta, Fujiwara, Yurie, Oda, Mitsunori
Format Journal Article
LanguageEnglish
Published Tokyo Japan Inst Heterocyclic Chemistry 31.12.2012
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Summary:8H-7,9-Bis(methoxycarbonyl)-5,11-methano[11]anuleno[c]furan-8-one (3) undergoes [4+3] cycloaddition with an oxyallyl species generated from 2,4-dibromo-3-pentanone in the presence of KI and copper, followed by dehydration in fluorosulfuric acid to give cyclohepta[11]annulenedione diester 9. After hydrolysis of the ester groups, decarboxylation yielded the title quinone 6. The H-1 NMR spectrum of 6 in D2SO4 indicates generation of its protonated dicationic species.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-12-S(N)75