Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Structure of Serratinidine and Fawcettidine. A New Type of Lycopodium Alkaloid
石井 永安井 凡平西野 隆一原山 尚犬伏 康夫
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1970 年 18 巻 9 号 p. 1880-1888

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Structures of two Lycopodium alkaloids, serratinidine (I) from Lycopodium serratum THUNB. var. serratum f. serratum and fawcettidine (XIX) from Lycopodium fawcettii LYLOYD et UNDERWOOD, were examined. In the previous papers, the authors suggested the biogenesis of serratinine and in connection of this, the skeletal structure ((B) in Chart 1) for serratinidine was selected as a working hypothesis. The validity of this assumption was shown by chemical correlation of serratinine ((C), R=OH, in Chart 1) of established structure with serratinidine through the route shown in Chart 2. On the other hand, fawcettidine was first isolated by Burnell from a Jamaican Lycopodium plant but since then there has been no report on the structure. From physical and spectral properties of this alkaloid appeared in the literature, the authors postulated the same skeletal structure for fawcettidine as that of serratinidine. Then, this assumption was proved by chemical conversion of serratinine into fawcettidine along the schemes shown in Chart 5. The present study reveals a new structural type of Lycopodium alkaloid.
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