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Synthesis of (−)-noranisatin, an oxidation product of a neurotoxic sesquiterpenoid anisatin having a novel spiro β-lactone

✍ Scribed by Haruki Niwa; Shigeki Ito; Takashi Hasegawa; Kazumasa Wakamatsu; Tatsuya Mori; Kiyoyuki Yamada


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
128 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis


The synthesis of (-)-noranisatin (2), an oxidation product of anisatin (1) possessing a novel Spiro P-lactone,was achieved starting from trio1 5 prepared from (R)-(+)-pulegone (3).

Anisatin (1) is a neurotoxic sesquiterpenoid isolated from the seeds of Japanese star anise (Illicium anisurum L., shikimi in Japanese). l.2 The structure of anisatin (1) was elucidated by extensive chemical and spectroscopic studies. Noranisatin (2), an oxidation product of anisatin (l), played an important role in the structural determination.2