Journal of Organic Chemistry 2015-01-16

Development of a Brønsted acid-promoted arene-ynamide cyclization toward the total syntheses of marinoquinolines A and C and aplidiopsamine A.

Yousuke Yamaoka, Takahiro Yoshida, Makiko Shinozaki, Ken-ichi Yamada, Kiyosei Takasu

Index: J. Org. Chem. 80(2) , 957-64, (2015)

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Abstract

A Brønsted acid-promoted arene-ynamide cyclization has been developed to construct the 3H-pyrrolo[2,3-c]quinolines. This reaction consists of the generation of a highly reactive keteniminium intermediate from arene-ynamide activated by a Brønsted acid and electrophilic aromatic substitution reaction to give arene-fused quinolines in high yields. This methodology enabled facile access to marinoquinolines A and C and aplidiopsamine A.