The photosensitized oxygenation of furanoeremophilanes. II. The preparation and stereochemistry of the isomeric hydroperoxides and the corresponding lactones from furanofukinin and furanoeremophilane.

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概要

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• The dye-sensitized oxygenation of furanofukinin, and furanoeremophilane, in methanol gave, quantitatively, crystalline mixtures of two isomeric hydroperoxides each consisting of a pair of 8α-methoxy-12β-hydroperoxy and 8β-methoxy-12α-hydroperoxy derivatives respectively. The hydroperoxides were readily transformed to the corresponding lactones with acetic anhydride-pyridine through dehydration. The stereochemistry of the hydroperoxides and the corresponding lactones has been elucidated by spectral and chemical methods according to a previously outlined generalization. Further, furanofukinin, furanoeremophilane, and 8β-hydroxyeremophilenolide, have been synthesized from petasalbin, fukinone, and an epimeric mixture of 8α- and 8β-methoxy lactones, respectively.

• 公益社団法人 日本化学会の論文

著者

• Naya Keizo

  Department of Chemistry, Faculty of Science, Kwansei Gakuin University

• Imagawa Takashi

  Department of Chemistry, Faculty of Science, Kwansei Gakuin University

• Nogi Noboru

  Department of Chemistry, Faculty of Science, Kwansei Gakuin University

• Makiyama Yasuo

  Department of Chemistry, Faculty of Science, Kwansei Gakuin University

• Takashina Hideo

  Department of Chemistry, Faculty of Science, Kwansei Gakuin University

関連論文

• Sesquiterpenes from the rhizomes of Ligularia dentata Hara.
• The Photosensitized Oxygenation of Furanoeremophilanes. I. The Isomeric Hydroperoxides from Petasalbin and Their Transformations to Lactones
• The photosensitized oxygenation of furanoeremophilanes. II. The preparation and stereochemistry of the isomeric hydroperoxides and the corresponding lactones from furanofukinin and furanoeremophilane.
• The transformations of terpene ketones by oxygen. I. The autoxidation of fukinone.
• The transformations of terpene ketones by oxygen. II. The base-catalyzed autoxidation of pulegone and fukinone and their dihydro compounds.
• The Structure of Petasitolone, a New Constituent of Petasites japonicus Maxim
• The Structural Elucidation of Sesquiterpene Lactones from Petasites japonicus Maxim
• The Preparation of Fukinane, A New Skeletal Sesquiterpene Hydrocarbon

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