Open AccessModular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade
Author(s) -
James A. RossiAshton,
Aimee K. Clarke,
Richard J. K. Taylor,
William P. Unsworth
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c00053
Subject(s) - chemistry , tryptamine , enantioselective synthesis , yield (engineering) , enantiomer , cascade , indole alkaloid , combinatorial chemistry , stereochemistry , alkaloid , enantiomeric excess , indole test , stereoisomerism , total synthesis , organic chemistry , catalysis , chromatography , biochemistry , materials science , metallurgy
The polycyclic core of the akuammiline alkaloids can be synthesized from simple tryptamine and tryptophol derivatives via a Ag(I)-catalyzed enantioselective dearomative cyclization cascade sequence. The complex tetracyclic scaffolds are prepared via a rapid, versatile, three-step modular synthesis from simple commercially available indole derivatives in high yields and enantiomeric excess (up to 99% yield and >99% ee ).
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