Synthesis and absolute configuration of 2-(12'-aminotridecyl)-pyrrolidine, a defensive alkaloid from the Mexican bean beetle, Epilachna varivestis

Article abstract of DOI:10.1016/0040-4020(96)00326-2

The synthesis of 2-(12'-aminotridecyl)-pyrrolidine (1), a defensive alkaloid recently isolated from the Mexican bean beetle, Epilachna varivestis, is described. The (2S,12'R) configuration is assigned to this alkaloid by comparing the ¹H NMR spectrum of its (S)-MTPA derivative with that of (R)- and (S)-MTPA [α-methoxy-α-(trifluoromethyl)phenylacetyl] derivatives of the synthetic sample. These results suggest that the seventeen carbon skeleton of 1 is acetate rather than proline derived.