Journal
ORGANIC LETTERS
Volume 15, Issue 9, Pages 2100-2103Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4004993
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- NIH (National Institute of General Medical Sciences) [R01GM092870]
- Vermont Genetics Network through INBRE Program of the National Institute of General Medical Sciences (NIGMS), a component of the National Institutes of Health (NIH) [8P20GM103449]
- National Science Foundation [CHE-1126265, CHE-0821501]
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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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