page_title: Samandarin
section_title: In the lab
hierarchical_section_title: Samandarin / Synthesis / In the lab
caption_attribution_description: English: Last steps of Shimizu's synthesis of ring A in samandarin
context_page_description: Samandarin or Samandarine is the main steroidal alkaloid secreted by the fire salamander. The compound is extremely toxic. Poisoning can cause convulsions, respiratory paralysis, and eventual death. Samandarin is also believed to be the active ingredient in Salamander brandy, a Slovenian drink with purported hallucinogenic and aphrodisiac effects.
context_section_description: The chemical synthesis of samandarin was of interest by a few groups in the 1960s and 1970s but has not been pursued in recent years. The construction of ring A was of greatest synthetic interest. Shimizu in 1976 was able to successfully construct the bridged oxazolidone system with correct stereoselectivity. The steps proceeded with low to moderate yields.
  The last few steps of the synthesis is shown below. Using m-chloroperobenzoic acid, an epoxide is created onto the alkene. The addition of sodium azide will facilitate the anti-Markovnikov opening of the epoxide. Reduction with sodium borohydride completes the azaheterocycle and bridged oxazolidone through either a cyclic amidine intermediate or imino ester intermediate.
caption: Last steps of Shimizu's synthesis of ring A in samandarin[7]
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