Enantioselective Total Synthesis of (+)-Stachyflin: A Potential Anti-Influenza A Virus Agent Isolated from a Microorganism

[摘要]：A novel and potent hemagglutinin inhibitor, (+)-stachyflin, was efficiently synthesized in an enantioselective manner starting from the (+)-5-methyl-Wieland-Miescher ketone. The synthetic method features a BF3 center dot Et2O-induced cascade epoxide-opening/rearrangement/cyclization reaction to stereoselectively construct the requisite pentacyclic ring system in one step. In order to rationalize the mechanism of the cascade reaction, quantum chemical calculations of the possible intermediary carbocations and transition states in the model synthesis were carried out. An alternative approach to synthesize (+)-stachyflin by employing a similar cascade reaction was also described.

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