Aldol condensation versus conjugate addition: Intramolecular cyclization using a combination of Lewis acid and 1,2-diol

DOI: 10.1248/cpb.48.1171

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1171 - 1175 (2000)

Update date:2022-08-05

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Authors:

Yamada Yamada

Suemune Suemune

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Article abstract of DOI:10.1248/cpb.48.1171

The reactivity of 3-substituted 4-methyl-4-(3-oxobutyl)-2-cyclohexen-1-ones (1) in the presence of a combination of a Lewis acid and a 1,2-diol was studied. The results suggest several factors that influence 6-membered ring formation, including two types of intramolecular aldol reaction and intramolecular 1,4-addition, due to the C3-substituent, Lewis acid, and the presence of diol. In this study, novel methodology to prepare two types of decalin skeleton could be developed.

Full text of DOI:10.1248/cpb.48.1171

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