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Articles • J. Braz. Chem. Soc. 10 (2) • 1999 • https://doi.org/10.1590/S0103-50531999000200007   copy

A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis

Authorship SCIMAGO INSTITUTIONS RANKINGS

This article presents the direct oxidation of limonene-oxide 1 with KIO4 in water, which is the best way to obtain the keto-aldehyde 3, an important intermediate in natural product synthesis. The cyclization of keto-aldehyde 3 with acidic Al2O3 proceeds chemoselectively to give ketone 4. These two reactions together increase the overall yield of ketone 4 to about 70% compared to 8% previously reported in the literature¹.

terpenoid chirons; epoxide ring opening; KIO4 oxidation; chemoselective cyclization

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