481656-29-5Relevant academic research and scientific papers
Enantioselective total synthesis of (+)-stachyflin: A potential anti-influenza a virus agent isolated from a microorganism
Sakurai, Junji,Kikuchi, Takuya,Takahashi, Ohgi,Watanabe, Kazuhiro,Katoh, Tadashi
, p. 2948 - 2957 (2011/06/26)
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 BF 3·Et2O-induced cascade epoxide-opening/ rearrangement/cyclization reaction tostereoselectively 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. A potential anti-influenza A virus agent, (+)-stachyflin, a novel hemagglutinin inhibitor, has been synthesized in an enantioselective manner for the first time starting from (+)-5-methyl-Wieland- Miescher ketone. The method features a BF3·Et 2O-induced cascade epoxide-opening/rearrangement/cyclization reaction to construct the requisite pentacyclic ring system in one step.
A New Strategy toward the Total Synthesis of Stachyflin, A Potent Anti-Influenza A Virus Agent: Concise Route to the Tetracyclic Core Structure
Nakatani, Mari,Nakamura, Masahiko,Suzuki, Akiyuki,Inoue, Munenori,Katoh, Tadashi
, p. 4483 - 4486 (2007/10/03)
(Matrix Presented) A new strategy directed toward the total synthesis of stachyflin, a potent and novel anti-influenza A virus agent isolated from a microorganism, has been presented through the enantioselective synthesis of the tetracyclic core structure. The synthetic method features a BF3·Et2O-induced domino epoxide-opening/rearrangement/cyclization reaction as the key step.
