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Total Synthesis of (−)‐Isoschizogamine
Author(s) -
Takada Akihiro,
Fujiwara Hiroaki,
Sugimoto Kenji,
Ueda Hirofumi,
Tokuyama Hidetoshi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503606
Subject(s) - aminal , quaternary carbon , total synthesis , claisen rearrangement , stereochemistry , chemistry , cascade , lactam , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , chromatography
The total synthesis of (−)‐isoschizogamine was accomplished, featuring the construction of the quaternary carbon center by the modified Johnson–Claisen rearrangement in basic media and the facile assembly of the key tetracyclic quinolone intermediate through a cascade cyclization. The characteristic cyclic aminal was constructed by late‐stage CH functionalization at the position adjacent to the lactam nitrogen using a combination of CrO 3 and n Bu 4 NIO 4 and subsequent Bi(OTf) 3 ‐mediated cyclization.