An Efficient Synthesis of 2,3,5,6-Tetramethylidene-7-oxanorbornane

Palladium‐catalyzed double carbomethoxylation of the Diels‐Alder adduct of furan and maleic anhydride yielded the methyl all‐exo‐7‐oxanorbornane‐2,3,5,6‐tetracarboxylate (7) which was transformed in three steps into 2,3,5,6‐tetramethylidene‐7‐oxanorbornane (1), a useful synthon. Six isomeric methyl...

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Veröffentlicht in:Helvetica chimica acta 1980-07, Vol.63 (5), p.1149-1157
Hauptverfasser: Mahaim, Cyril, Carrupt, Pierre-Alain, Hagenbuch, Jean-Pierre, Florey, André, Vogel, Pierre
Format: Artikel
Sprache:eng
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Zusammenfassung:Palladium‐catalyzed double carbomethoxylation of the Diels‐Alder adduct of furan and maleic anhydride yielded the methyl all‐exo‐7‐oxanorbornane‐2,3,5,6‐tetracarboxylate (7) which was transformed in three steps into 2,3,5,6‐tetramethylidene‐7‐oxanorbornane (1), a useful synthon. Six isomeric methyl 7‐oxanor‐bornane‐2,3,5,6‐tetracarboxylates (7–12) have been isolated and their 1H‐ and 13C‐NMR. data are compared.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.19800630506