Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 21, Pages 7713-7715Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500185
Keywords
aromatic ring umpolung; hypervalent iodine; natural products; oxidation; total synthesis
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- provincial government of Quebec (FQRNT and CCVC)
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Althought there are several reported synthetic routes to strychnine, one of the most widely recognized alkaloids, we report an unexplored route with an oxidative dearomatizing process mediated by hypervalent iodine as the key step. The new syntheses of isostrychnine and strychnine have been achieved from an readily available phenol in nine and ten steps. In addition to the key step, these syntheses involve an aza Michael-ether-enol tandem transformation, two heck type cyclizations, a reductive isomerization, and a double reductive amination in cascade leading to the alkaloid main core.
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