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Org Lett. 2013 May 3;15(9):2100-3. doi: 10.1021/ol4004993. Epub 2013 Apr 15.

Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.

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  • 1The University of Vermont, 82 University Place, Burlington, Vermont 05405, United States.


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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