Facile Construction of Furan-Fused Methano[11]annulenone Skeleton by Successive Aldol Condensations from 3,4-Furandicarbaldehydes
作者:Shigeyasu Kuroda、Yanmei Zhang、Nobuhiko Takezawa、Yosikazu Horino、Ayumi Takai、Yasutomo Tsuji、Ryuta Miyatake、Mitsunori Oda
DOI:10.3987/com-08-s(f)52
日期:——
Aldol condensation of furan-3,4-dicarbaldehyde with pentanedial in acetic acid gave 6H-cyclohepta[c]furan-5,7-dicarbaldehyde in a good yield. Then, successive condensation of 6H-cyclohepta[c]furan-5,7-dicarbaldehyde with dimethyl 1,3 -acetonedicarboxylate under azeotropic conditions gave a diester derivative of furan-fused methano[11]annulenone also in a good yield. The hydrolysis of the diester groups and subsequent decarboxylation provided a non-substituted furan-fused methano[11]annulenone. A similar sequence starting from 2,5-dimethylfuran-3,4-dicarbaldehyde gave its dimethyl derivative. Cycloaddition and protonation of these furan-fused methano[11]annulenones were also studied.