Formal synthesis of (-)-podophyllotoxin through the photocyclization of an axially chiral 3,4-bisbenzylidene succinate amide ester--a flow photochemistry approach.

@article{Lisiecki2016FormalSO,
  title={Formal synthesis of (-)-podophyllotoxin through the photocyclization of an axially chiral 3,4-bisbenzylidene succinate amide ester--a flow photochemistry approach.},
  author={Kamil Lisiecki and Krzysztof K. Krawczyk and Piotr I. Roszkowski and Jan K Maurin and Zbigniew Czarnocki},
  journal={Organic \& biomolecular chemistry},
  year={2016},
  volume={14 2},
  pages={
          460-469
        }
}
We have developed a strategy for the stereoselective synthesis of cyclolignans related to podophyllotoxin and its derivatives. The crucial step of the synthesis is the photocyclization of a chiral atropoisomeric 1,2-bisbenzylidenesuccinate amide ester, which can be prepared from suitable aromatic aldehydes, diethyl succinate and l-prolinol. The photocyclization was found to be more efficient when irradiation was performed in a home-built continuous flow photochemical reactor. The in-flow… 
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