A concise synthesis of turneforcidine via a metalloiminium ion cyclization terminated by the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl moiety.
A concise synthetic route to racemic turneforcidine (1) is described that relies on the stereocontrolled cyclization of the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl bearing imine 5 in the presence of TiCl(4). Reaction: see text.
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Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
Duncan
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D
Livinghouse
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Reid
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D007097:Imines / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D014025:Titanium / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis
C433404:2-(thiomethyl)-3-trimethylsilyl-1-propenyl; D007097:Imines; D011763:Pyrrolizidine Alkaloids; D014297:Trimethylsilyl Compounds; C443726:turneforcidine; C025096:titanium tetrachloride; D014025:Titanium