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^*

^*この論文の責任著者

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

19 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	16400-16403
ページ数	4
ジャーナル	Chemistry - A European Journal
巻	21
号	46
DOI	https://doi.org/10.1002/chem.201503606
出版ステータス	出版済み - 2015/11/01

ASJC Scopus 主題領域

触媒
有機化学

文献へのアクセス

10.1002/chem.201503606

引用スタイル

@article{d8117b1a5467461ba0473716c3343e4c,

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",

month = nov,

day = "1",

doi = "10.1002/chem.201503606",

language = "英語",

volume = "21",

pages = "16400--16403",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "46",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=84945912982&partnerID=8YFLogxK

U2 - 10.1002/chem.201503606

DO - 10.1002/chem.201503606

M3 - 学術論文

C2 - 26663535

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

抄録

ASJC Scopus 主題領域

文献へのアクセス

フィンガープリント

引用スタイル