Issue 18, 2019

Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy

Abstract

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.

Graphical abstract: Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy

Supplementary files

Article information

Article type
Paper
Submitted
27 Mar 2019
Accepted
27 Mar 2019
First published
03 Apr 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 10420-10424

Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy

T. Itoh, Y. Chiba, S. Kawaguchi, Y. Koitaya, Y. Yoneta, K. Yamada and T. Abe, RSC Adv., 2019, 9, 10420 DOI: 10.1039/C9RA02321F

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