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A novel manzamine-related alkaloid consisting of unprecedented 8/5/5/5/15/6 ring system, nakadomarin A ( 1 ), has been isolated from an Okinawan marine sponge Amphimedon sp., and the unique structure containing a furan ring was elucidated on the basis of the spectroscopic data. The relative stereochemistry was deduced from the NOE data and proton couplings, and a plausible biogenetic path of 1 through ircinal A was proposed.
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Kobayashi et al. (1997) studied this question.
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