A novel method for the conversion of saturated pyrrolizidine esters into their 1,2-didehydro-derivatives has been established. The unsaturation is introduced by phenylselenenylation α to an ester function, followed by fragmentation of the derived seleno-derivative. Using this technique, (±)-supinidine (1) has been synthesized.
D. J. Robins and S. Sakdarat, J. Chem. Soc., Perkin Trans. 1, 1979, 1734 DOI: 10.1039/P19790001734
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