Synthesis of (±)-β-Cuparenone Based on a Lewis Acid-Promoted [4++2] Polar Cycloaddition of m-Tolylthiomethyl Chloride

Hiroyuki ISHIBASHI; Hiroshi NAKATANI; Duk Jae CHOI; Maromi TAGUCHI; Masazumi IKEDA

doi:10.1248/cpb.38.1738

Synthesis of (±)-β-Cuparenone Based on a Lewis Acid-Promoted [4⁺+2] Polar Cycloaddition of m-Tolylthiomethyl Chloride

Hiroyuki ISHIBASHI, Hiroshi NAKATANI, Duk Jae CHOI, Maromi TAGUCHI, Masazumi IKEDA

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Keywords: (±)-β-cuparenone, α-chlorosulfide, polar cycloaddition, hydroxylation, oxidative glycol cleavage, oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide), desulfurization, sodium metaperiodate, zinc dust

JOURNAL FREE ACCESS

1990 Volume 38 Issue 6 Pages 1738-1739

DOI https://doi.org/10.1248/cpb.38.1738

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Abstract

In the presence of AlCl₃, m-tolylthiomethyl chloride (1) reaceted with methyl 3, 4-dimetylcyclopent-3-ene-1-carboxylate (4) to give the [4⁺+2] polar cycloadditino product 6, which was transformed into (±)-β-cuparenone (11) in 4 steps.

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