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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| Format | Journal Article |
| Language | English |
| Published |
03.04.2019
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| 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.
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. |
|---|---|
| AbstractList | 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. |
| Author | Koitaya, Yuki Abe, Takumi Kawaguchi, Shunsuke Chiba, Yuusuke Yamada, Koji Itoh, Tomoki Yoneta, Yuuma |
| AuthorAffiliation | Faculty of Pharmaceutical Sciences Health Sciences University of Hokkaido |
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| Author_xml | – sequence: 1 givenname: Tomoki surname: Itoh fullname: Itoh, Tomoki – sequence: 2 givenname: Yuusuke surname: Chiba fullname: Chiba, Yuusuke – sequence: 3 givenname: Shunsuke surname: Kawaguchi fullname: Kawaguchi, Shunsuke – sequence: 4 givenname: Yuki surname: Koitaya fullname: Koitaya, Yuki – sequence: 5 givenname: Yuuma surname: Yoneta fullname: Yoneta, Yuuma – sequence: 6 givenname: Koji surname: Yamada fullname: Yamada, Koji – sequence: 7 givenname: Takumi surname: Abe fullname: Abe, Takumi |
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| Title | 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 |
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