Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Spirostomin, Defense Toxin of the Ciliate Spirostomum teres: Isolation, Structure Elucidation, and Synthesis
Yoshihiko SeraMiyuki Eiraku MasakiMatsumi DoeFederico BuonannoAkio MiyakeYoshinosuke UsukiHideo Iio
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JOURNALS RESTRICTED ACCESS Advance online publication

Article ID: 150044


The defense toxins, spirostomins A and B, have been isolated as a diastereomeric mixture from the ciliate microorganism Spirostomum teres. The structure of spirostomin was elucidated through a number of NMR experiments which allowed assigning the unprecedented spiro[(2,5-dimethyl-5,6,7,8-tetrahydronaphthalene-1,4-dione)-8,6'-(pyrane-2',5'-dione)] skeleton to this natural compound. The total syntheses of the racemic spirostomins confirmed their structure and relative configurations.

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