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Enantioselective Total Synthesis of (+)‐Stachyflin: A Potential Anti‐Influenza A Virus Agent Isolated from a Microorganism
Author(s) -
Sakurai Junji,
Kikuchi Takuya,
Takahashi Ohgi,
Watanabe Kazuhiro,
Katoh Tadashi
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100173
Subject(s) - enantioselective synthesis , chemistry , cascade reaction , total synthesis , ketone , stereochemistry , carbocation , combinatorial chemistry , cascade , epoxide , chemical synthesis , organic chemistry , catalysis , biochemistry , chromatography , in vitro
Abstract 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 · Et 2 O‐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.