The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxidation and a subsequent unexpected protecting-group migration. This total synthesis revealed that the reported structure of the naturally isolated compound is incorrect.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5716997 | PMC |
| http://dx.doi.org/10.1038/s41598-017-17015-8 | DOI Listing |
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