Total Synthesis of (-)-Isoschizogamine

被引：18

作者：

Takada, Akihiro ^{[1
]}

Fujiwara, Hiroaki ^{[1
]}

Sugimoto, Kenji ^{[1
]}

Ueda, Hirofumi ^{[1
]}

Tokuyama, Hidetoshi ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 46期

关键词：

alkaloids; aminal; cascade reaction; CH functionalization; total synthesis; AUS SCHIZOZYGIA CAFFAEOIDES; C-H OXIDATION; CATALYZED OXIDATION; REVISED STRUCTURE; ISOSCHIZOGAMINE; EFFICIENT; ALKALOIDS; FUNCTIONALIZATION; CYCLIZATION; METATHESIS;

D O I：

10.1002/chem.201503606

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 CrO3 and nBu(4)NIO(4) and subsequent Bi(OTf)(3)-mediated cyclization.

引用

页码：16400 / 16403

页数：4

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