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Total Synthesis of Dictyodendrins A–F by the Gold‐Catalyzed Cascade Cyclization of Conjugated Diyne with Pyrrole
Author(s) -
Matsuoka Junpei,
Inuki Shinsuke,
Matsuda Yuka,
Miyamoto Yoichi,
Otani Mayumi,
Oka Masahiro,
Oishi Shinya,
Ohno Hiroaki
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001950
Subject(s) - conjugated system , carbazole , pyrrole , annulation , catalysis , cascade , chemistry , combinatorial chemistry , total synthesis , stereochemistry , organic chemistry , polymer , chromatography
The total synthesis of dictyodendrins A–F was achieved by using the gold(I)‐catalyzed annulation of a conjugated diyne with N ‐Boc‐pyrrole for direct construction of the pyrrolo[2,3‐ c ]carbazole scaffold. Late‐stage functionalization of the resulting pyrrolo[2,3‐ c ]carbazole to introduce various substituents provided divergent access to dictyodendrins. Some dictyodendrin analogues exhibited inhibitory activities toward CDK2/CycA2 and GSK3.