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Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine
Author(s) -
De Simone Filippo,
Gertsch Jürg,
Waser Jérôme
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201001853
Subject(s) - total synthesis , indole test , position (finance) , chemistry , computer science , catalysis , formal synthesis , combinatorial chemistry , stereochemistry , organic chemistry , business , finance
Mild control : Selective cyclization of aminocyclopropanes at either the N1 or C3 position of an indole ring was achieved by tuning the reaction conditions (see scheme). This strategy was applied to the formal synthesis of aspidospermidine and the total synthesis of goniomitine, which demonstrated significant cytotoxicity against several tumor cell lines (IC 50 =150–400 n M ). Cbz=benzyloxycarbonyl, Ts=4‐toluenesulfonyl.