Puffer Fish Poison Synthesis
Filed In Poisons
In our project directed toward the total syntheses of tetrodotoxin and its natural and unnatural analogues, we have recently completed the syntheses of 5,11–dideoxytetrodotoxin,13 11–deoxytetrodotoxin,14 and 8,11–dideoxytetrodotoxin15 in enantiomerically pure form on the basis of a Diels–Alder strategy from levoglucosenone. Among them, 11–deoxytetrodotoxin was the first total synthesis of a naturally occurring tetrodotoxin analogue. The full details of the total synthesis of tetrodotoxin (1) are described here on a different basic strategy aiming at a higher oxidation stage in earlier stages of the synthesis.