The Photosensitized Oxygenation of Furanoeremophilanes. II. The Preparation and Stereochemistry of the Isomeric Hydroperoxides and the Corresponding Lactones from Furanofukinin and Furanoeremophilane
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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DOI：
10.1246/bcsj.50.3002
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发表时间：
1977-11
影响因子：
4
通讯作者：
K. Naya;Noboru Nogi;Yasuo Makiyama;H. Takashina;T. Imagawa
中科院分区：
文献类型：
--
作者：
K. Naya;Noboru Nogi;Yasuo Makiyama;H. Takashina;T. Imagawa
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.
