PleaseC dh oe mn oi ct a al dS cj ui es nt cme argins
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Journal Name
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For selected syntheses of spirocyclic indoles, see: (a) T.
Conclusion
Deng, W. Mazumdar, R. L. Ford, N. Jana, R. Izar, D. J. Wink
DOI: 10.1039/D0SC03676E
A concise and divergent approach to 1-azaspiro[4,4]nonane
derivatives, which features a novel sodium naphthalenide-
mediated reductive-HWE cascade reaction, has been
developed. By variation of the alkyne, the phosphonate ester,
and the pyrrolidine backbone, a large class of highly
substituted and densely functionalised spirocyclic pyrrolidines
was constructed, significantly broadening the synthetic access
to this chemical space. We believe the modularity of this
sequence lends itself well to applications in medicinal
chemistry and natural product synthesis alike. To this end, the
utility of the reaction pathway was demonstrated by its
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successful application in
a
formal synthesis of (±)-
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,
8
39–844. (i) R. Saruengkhanphasit, D. Collier and I. Coldham,
cephalotaxine, accessing Mori’s tetracyclic intermediate in
only 7 steps. Furthermore, this work demonstrates and opens
up the underexploited paradigm of deploying isoxazolines as
masked ketone equivalents in reductive cascade sequences.
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, 9739–9745. For spirocyclic pyrrole
Conflicts of interest
There are no conflicts to declare.
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S. L. You, Angew. Chemie - Int. Ed., 2015, 54, 8475–8479.
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Acknowledgements
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,
P. W. S. is grateful to the EPSRC Centre for Doctoral Training in
Synthesis for Biology and Medicine [EP/L015838/1] for a
studentship, generously supported by AstraZeneca, Diamond
Light Source, Defence Science and Technology Laboratory,
Evotec, GlaxoSmithKline, Janssen, Novartis, Pfizer, Syngenta,
Takeda, UCB and Vertex. Y. O. thanks the EC for IIFs [PIIF-GA-2012-
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