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In summary, we have developed a novel, efficient synthesis
of fused indolizinones from cyclopropyl ketones and nitriles
using a Lewis acid–copper(I) binary catalytic system, which
involves the Lewis acid-triggered ring-opening reaction of
cyclopropyl ketones with nitriles, copper(I)-catalyzed Ritter
process, and acid-promoted N-acyliminium ion cyclization
sequence. This protocol features a broad substrate scope and
excellent functional-group tolerance and shows potential capabilities
to construct complex molecules in synthetic and pharmaceutical
chemistry, as notably bioactive crispine A was successfully
synthesized in two steps with comparable overall yield by the
key transformation. Further studies on the asymmetric version
of this methodology are currently in progress and will be
reported in due course.
This work was supported by the National Natural Science
Foundation of China (20932002 and 21172076), the National Basic
Research Program of China (973 Program) (2011CB808600), the
Guangdong Natural Science Foundation (10351064101000000)
and the Fundamental Research Funds for the Central Universities
(2010ZP0003).
Notes and references
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c
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Chem. Commun.