Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategyElectronic supplementary information (ESI) available: Detailed experimental procedures and spectra data for all compounds, including scanned images of 1H and 13C NMR spectra. See DOI: 10.1039/c9ra02321f

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...

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Main Authors Itoh, Tomoki, Chiba, Yuusuke, Kawaguchi, Shunsuke, Koitaya, Yuki, Yoneta, Yuuma, Yamada, Koji, Abe, Takumi
Format Journal Article
LanguageEnglish
Published 03.04.2019
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Summary: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. The regioselective synthesis of pyrano[3,2- e ]indole alkaloid fontanesine B have been accomplished by C4 Pictet-Spengler cyclization and Bischler-Napieralski-type cyclization of a trichloromethyl carbamate.
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Electronic supplementary information (ESI) available: Detailed experimental procedures and spectra data for all compounds, including scanned images of
10.1039/c9ra02321f
C NMR spectra. See DOI
ISSN:2046-2069
DOI:10.1039/c9ra02321f