31 Thujopseneの転位

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概要

• 論文の詳細を見る

• Treatment of the tricyclic sequiterpene thujopsene (1) with mild acid (0.02M HClO_4 in refluxing 80% aqueous dioxane) gives widdrol (2) as the initial product. Similar treatment of the trans-thujopsene (4) yields epi-widdrol (5) as the initial product. The prolonged heating of the reaction mixture results in the formation of the diene 3 from thujopsene and the diene 6 from the trans-thujopsene. These results indicate that under the mildly acidic conditions, stereochemical integrity of the cyclopropylcarbinyl system is preserved. However, under the strongly acidic conditions, namely 0.02M HClO_4 in refluxing acetic acid, both cis thujopsene and the diene 6 yield a mixture of three hydrocarbons 9, 10 and 11. The structure of the major hydrocarbon 9 was reported previously. The structures of the two minor compounds 10 and 11 are reported here.

• 天然有機化合物討論会の論文
• 1970-10-01

著者

• Dauben William

  Department Of Chemistry University Of California

• Aoyagi Edward

  Department of Chemistry University of California

• Aoyagi Edward

  Department Of Chemistry University Of California:national Institutes Of Health Predoctoral Fellow

関連論文

• E-5-4 Synthesis and Ultraviolet Spectra of 4,5-Methylenesteroids and Related Compounds(Mainly physico-chemical methods)
• 31 Thujopseneの転位

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