Total Synthesis of (−)‐Isoschizogamine | Zendy

Takada Akihiro | Zendy; Fujiwara Hiroaki | Zendy; Sugimoto Kenji | Zendy; Ueda Hirofumi | Zendy; Tokuyama Hidetoshi | Zendy

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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.

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