TY - JOUR
T1 - Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis
AU - Shi, Xiongwei
AU - Attygalle, Athula B.
AU - Meinwald, Jerrold
PY - 1997/9/15
Y1 - 1997/9/15
N2 - Syntheses of (2S,12'R)-2-(12'-aminotridecyl)-pyrrolidine (1) and (28,12'R)-1-(2'-hydroxyethyl)-2-(12'-aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of 1H 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 1H NMR investigation of(2S,12'S)-1, (2S,12'S)-2, and their MTPA derivatives.
AB - Syntheses of (2S,12'R)-2-(12'-aminotridecyl)-pyrrolidine (1) and (28,12'R)-1-(2'-hydroxyethyl)-2-(12'-aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of 1H 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 1H NMR investigation of(2S,12'S)-1, (2S,12'S)-2, and their MTPA derivatives.
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U2 - 10.1016/S0040-4039(97)01491-3
DO - 10.1016/S0040-4039(97)01491-3
M3 - Article
AN - SCOPUS:0030864567
SN - 0040-4039
VL - 38
SP - 6479
EP - 6482
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 37
ER -