TY - JOUR
T1 - Absolute configuration of insect-produced epilachnene
AU - Farmer, Jay J.
AU - Attygalle, Athula B.
AU - Smedley, Scott R.
AU - Eisner, Thomas
AU - Meinwald, Jerrold
PY - 1997/4/21
Y1 - 1997/4/21
N2 - Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.
AB - Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.
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U2 - 10.1016/S0040-4039(97)00490-5
DO - 10.1016/S0040-4039(97)00490-5
M3 - Article
AN - SCOPUS:0343196694
SN - 0040-4039
VL - 38
SP - 2787
EP - 2790
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 16
ER -