A Two-Directional Synthesis of (+/-)-Perhydrohistrionicotoxin

Stockman, Robert, Sinclair, Alex, Arini, Louise, Szeto, Peter and Hughes, David (2004) A Two-Directional Synthesis of (+/-)-Perhydrohistrionicotoxin. The Journal of Organic Chemistry, 69(5), pp. 1598-1602. ISSN (print) 0022-3263


An entirely two-directional synthesis of (+/-)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (+/-)-histrionicotoxin and (+/-)-histrionicotoxin 235A.

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