25074-12-8Relevant articles and documents
Weinheimer,Washecheck
, p. 3315 (1969)
New Route for Synthesis of Furan Derivatives from Protected α-Ketols and Ketones. A Total Synthesis of Furoventalene
Hagiwara, Hisahiro,Uda, Hisashi
, p. 91 - 94 (2007/10/02)
Reaction of acetonyl tetrahydropyranyl ether (1) with ketones (2a-d) in the presence of lithium di-isopropylamide and zinc chloride produces the cross-aldol condensation products (3a-d), which are transformed into 3-methylfurans (4a-d), by treatment with
Regioselective Total Synthesis of Furoventalene, a Marine Natural Benzofuran, via the β-Vinylbutenolide Annulation
Kido, Fusao,Noda, Yoshihiro,Maruyama, Takao,Kabuto, Chizuko,Yoshikoshi, Akira
, p. 4264 - 4266 (2007/10/02)
The framework of furoventalene (1) was regioselectively constructed from methyl 2-formyl-6-methyl-5-heptenoate (12) and 2,5-dihydro-3-methyl-4-vinyl-2-furanone (10) by consecutive 1,6 conjugate addition and aldol-type cyclization to lead to a diastereomeric mixture of bicyclic butenolides 13a and 13b.Both of the annulation products were transformed into 1 by a sequence of reactions: reduction, hydrolysis, dehydrative decarboxylation, and dehydrogenation via intermediates 14-16.The stereochemistry of the annulation products 13a and 13b is also discussed.