DEFENSIVE-MECHANISMS OF ARTHROPODS .144. ABSOLUTE-CONFIGURATION OF INSECT-PRODUCED EPILACHNENE

Authors
FARMER JJ ATTYGALLE AB SMEDLEY SR EISNER T MEINWALD J
Citation
Jj. Farmer et al., DEFENSIVE-MECHANISMS OF ARTHROPODS .144. ABSOLUTE-CONFIGURATION OF INSECT-PRODUCED EPILACHNENE, Tetrahedron letters, 38(16), 1997, pp. 2787-2790
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
16
Year of publication
1997
Pages
2787 - 2790
Database
ISI
SICI code
0040-4039(1997)38:16<2787:DOA.AO>2.0.ZU;2-D
Abstract
Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec -5-en-14-olide] were synthesized from (R) and(S)-norvaline. The diaste reomeric alpha-methoxy-alpha-trifluoromethylphenylacetyl amides of the se synthetic samples, prepared using (S) alpha-methoxy-alpha-trifluoro methylphenylacetyl 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, Ep ilachna varivestis, established that the natural product is (S)-epilac hnene. (C) 1997 Elsevier Science Ltd.