Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
2019
Itoh, Tomoki | Chiba, Yuusuke | Kawaguchi, Shunsuke | Koitaya, Yuki | Yoneta, Yuuma | Yamada, Koji | Abe, Takumi
The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were constructed by a new Bischler–Napieralski-type cyclization, in which an unprecedented trichloromethyl carbamate serves as a reactive group.
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