Total Synthesis of (-)-Isoschizogamine

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

doi:10.1002/chem.201503606

Total Synthesis of (-)-Isoschizogamine

Akihiro Takada, Hiroaki Fujiwara, Kenji Sugimoto, Hirofumi Ueda, Hidetoshi Tokuyama^*

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

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 C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO₃ and nBu₄NIO₄ and subsequent Bi(OTf)₃-mediated cyclization.

Original language	English
Pages (from-to)	16400-16403
Number of pages	4
Journal	Chemistry - A European Journal
Volume	21
Issue number	46
DOIs	https://doi.org/10.1002/chem.201503606
State	Published - 2015/11/01

Keywords

C-H functionalization
alkaloids
aminal
cascade reaction
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201503606

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title = "Total Synthesis of (-)-Isoschizogamine",

abstract = "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 C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.",

keywords = "C-H functionalization, alkaloids, aminal, cascade reaction, total synthesis",

author = "Akihiro Takada and Hiroaki Fujiwara and Kenji Sugimoto and Hirofumi Ueda and Hidetoshi Tokuyama",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

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doi = "10.1002/chem.201503606",

language = "英語",

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journal = "Chemistry - A European Journal",

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T1 - Total Synthesis of (-)-Isoschizogamine

AU - Takada, Akihiro

AU - Fujiwara, Hiroaki

AU - Sugimoto, Kenji

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

PY - 2015/11/1

Y1 - 2015/11/1

N2 - 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 C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.

AB - 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 C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.

KW - C-H functionalization

KW - alkaloids

KW - aminal

KW - cascade reaction

KW - total synthesis

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U2 - 10.1002/chem.201503606

DO - 10.1002/chem.201503606

M3 - 学術論文

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AN - SCOPUS:84945912982

SN - 0947-6539

VL - 21

SP - 16400

EP - 16403

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 46

ER -

Total Synthesis of (-)-Isoschizogamine

Abstract

Keywords

ASJC Scopus subject areas

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