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Synthesis 2000; 2000(14): 2099-2105
DOI: 10.1055/s-2000-8733
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Asymmetric Total Synthesis of (+)-2-epi-Deoxoprosopinine

Dieter Enders* , Jan H. Kirchhoff
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax +49(241)8 88 81 27; E-mail: Enders@RWTH-Aachen.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The asymmetric synthesis of (+)-2-epi-deoxoprosopinine [(S,S,R)-5] in eleven steps and with excellent diastereomeric and enantiomeric purity (de, ee ≥96%) is described. As key steps, the 1,2-addition of a dodecyl nucleophile to an aldehyde-SAMP hydrazone and the α-alkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP hydrazone are employed to generate two of the three stereogenic centers. Creation of the third stereogenic center was achieved in a domino deprotection/cyclisation/reduction sequence.

asymmetric synthesis - deoxoprosopinine - SAMP/RAMP hydrazone method - natural products - piperidine alkaloids

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