A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3671602 | PMC |
| http://dx.doi.org/10.1021/ol4004993 | DOI Listing |
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