A Hawaiian fish called the pahu or boxfish (Ostracian lentiginosus) secretes a toxin that kills other fish in its vicinity. The active agent in the secretion was named pahutoxin by P. J. Scheuer, and it was found by D. B. Boylan and Scheuer to contain an unusual combination of lipid moieties. To prove its structure, they synthesized it by this route:

What are the structures of A, C, D, and E and of pahutoxin?

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он о pyridinium BrCH2C02Et,Zn (1) HO (2) H2O OEt chlorochromate 12 SOC2 choline chloride utoxin Selected Infrared Absorption Bands (cm ) 1725 3300 (broad), 1735 3300-2500 (broad), 1710 3000-2500 (broad), 1735, 1710 1800, 1735 1735 Compound Pahutoxin