Journal of Organic Chemistry p. 4264 - 4266 (1981)
Update date:2022-08-05
Topics:
Kido, Fusao
Noda, Yoshihiro
Maruyama, Takao
Kabuto, Chizuko
Yoshikoshi, Akira
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.
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Doi:10.1016/S0040-4020(01)91531-5
(1984)Doi:10.1021/jo00335a013
(1981)Doi:10.1016/j.carres.2008.03.002
(2008)Doi:10.1002/cjoc.201180382
(2011)Doi:10.1021/jo01375a017
(1954)Doi:10.1007/BF00759467
(1981)
