Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis

✍ Scribed by Xiongwei Shi; Athula B. Attygalle; Ferrold Meinwald

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 235 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01491-3

✦ Synopsis

Syntheses of (2S, 12' R)-2-( 12' -aminotridecyl)-pyrrolidine ( 1 ) and (2S, 12' R)-I -(2' '-hydroxyethyl)-2-(l 2'aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of IH NMR data of MTPA derivatives of natural alkaloid 2 with those of the synthetic standard, we confirm the (2S,12'R) configuration previously suggested for this alkaloid. Further support of these assignments was provided by the synthesis and J H NMR investigation of (2S,12'S)-1, (2S, 12'S)-2, and their MTPA derivatives.