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Synthesis 2000; 2000(4): 510-512
DOI: 10.1055/s-2000-6379
short paper
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Efficient Synthesis of (2S,12′R)-2-(12′-Aminotridecyl)pyrrolidine: A Defense Alkaloid of the Mexican Bean Beetle

Dieter Enders* , Christoph Thiebes
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax +49 (2 41) 8 88 81 27; E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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The synthesis of (2S,12′R)-2-(12′-aminotridecyl)pyrrolidine [(S,R)-8], a defense alkaloid of the Mexican bean beetle Epilachna varivestis starting from (R)-proline is described. The second stereogenic center is generated by nucleophilic 1,2-addition of methyllithium to an aldehyde-SAMP-hydrazone, followed by reductive N-N bond cleavage. The product is obtained in good yield and high enantiomeric and diastereomeric purity.

natural products - asymmetric synthesis - alkaloids - nucleophilic 1,2-addition - SAMP/RAMP hydrazone method - pyrrolidines

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