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.

SUBMITTER: Itoh T 

PROVIDER: S-EPMC9062488 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature