TY - JOUR
T1 - Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade
T2 - Application to Total Synthesis of (+)-Pestalazine B
AU - Hakamata, Hiroyuki
AU - Ueda, Hirofumi
AU - Tokuyama, Hidetoshi
N1 - Funding Information:
This work was supported by the Drug Discovery and Life Science Research (BINDS) from AMED under Grant Nos. JP18am0101100 and JSPS KAKENHI Grant Nos. JP18H04379 in Middle Molecular Strategy, JP18H04231 in Precisely Designed Catalysts with Customized Scaffolding, and JP18H04642 in Hybrid Catalysis and Grants-in-aid for Scientific Research (B) (18H02549) and (C) (17K08204).
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/6/7
Y1 - 2019/6/7
N2 - An N-linked indole structure was constructed on the 3a-position of pyrroloindoline derivatives via a cascade process involving silver-mediated amination of bromopyrroloindolines with 2-ethynylanilines with subsequent 5-endo-dig cyclization. In this reaction, AgNTf2 was used as a tandem reagent, which activated the bromo group as a σ-Lewis acid and the alkyne moiety as a π-Lewis acid. Switching from the initial step to the second step was conducted by controlling the temperature. This protocol was applied to the synthesis of various pyrroloindolines, α-carboline, and furoindolines and the total synthesis of a dimeric indole alkaloid, (+)-pestalazine B.
AB - An N-linked indole structure was constructed on the 3a-position of pyrroloindoline derivatives via a cascade process involving silver-mediated amination of bromopyrroloindolines with 2-ethynylanilines with subsequent 5-endo-dig cyclization. In this reaction, AgNTf2 was used as a tandem reagent, which activated the bromo group as a σ-Lewis acid and the alkyne moiety as a π-Lewis acid. Switching from the initial step to the second step was conducted by controlling the temperature. This protocol was applied to the synthesis of various pyrroloindolines, α-carboline, and furoindolines and the total synthesis of a dimeric indole alkaloid, (+)-pestalazine B.
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U2 - 10.1021/acs.orglett.9b01399
DO - 10.1021/acs.orglett.9b01399
M3 - Article
C2 - 31117711
AN - SCOPUS:85067085111
SN - 1523-7060
VL - 21
SP - 4205
EP - 4209
JO - Organic Letters
JF - Organic Letters
IS - 11
ER -