Efficient Synthesis of (2S,12′R)-2-(12′-Aminotridecyl)pyrrolidine: A Defense Alkaloid of the Mexican Bean Beetle
- 31 December 2000
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2000 (04) , 510-512
- https://doi.org/10.1055/s-2000-6379
Abstract
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.Keywords
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