Total synthesis of (+/-)-monomorine I and (+/-)-indolizidine 195B by an aza-[2,3]-Wittig rearrangement of a vinylaziridine.
A novel synthesis of (+/-)-monomorine I (1) and (+/-)-indolizidine 195B (2) is described in which the key step is the highly efficient aza-[2,3]-Wittig rearrangement of vinylaziridine 12 into tetrahydropyridine 13. Functional group manipulation then gave ketone 16 which could be converted into the target alkaloids by reductive amination (1:2 1.5:1).
Somfai
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P
Organic Chemistry 2, Lund Institute of Technology, Lund University, Sweden.
Jarevång
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T
Lindström
U M
UM
Svensson
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A
D000818:Animals; D001372:Aza Compounds / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy
D001372:Aza Compounds; D007212:Indolizines; C110223:indolizidine-195B