Journal
CHEMISTRYSELECT
Volume 7, Issue 31, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202202703
Keywords
Acylation; Aromatic substitution; Bronsted acid catalysis; Nitrogen heterocycles; Synthetic methods
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Funding
- University of Bath
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Pancratistatin framework can be accessed through a concise synthetic route without the need for metal catalysis or activated substrates. This method offers the possibility of generating various pancratistatin analogues for further development.
Pancratistatin and narciclasine are natural products that display potent and selective antiproliferative activity against various cancer cells. We explore convergent synthetic routes to access the pancratistatin framework in just two steps, without the need for metal catalysis or activated substrates via a common indanone intermediate. The indanone is synthesised by intermolecular Friedel-Crafts acylation with trifluoroacetic acid anhydride (TFAA), by two alternative routes, and then undergoes a Schmidt reaction with TFA to generate the pancratistatin core. This concise approach offers the possibility of generating various pancratistatin analogues for further development.
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