ABSOLUTE-CONFIGURATION OF THE POLYAZAMACROLIDES, MACROCYCLIC POLYAMINES PRODUCED BY A LADYBIRD BEETLE

The absolute configuration of the polyazamacrolides, oligomeric macroc ycles from the pupal defensive secretion of Epilachna borealis, was de termined by comparison of derivatives of the natural material with ena ntiomerically pure synthetic samples. Samples of a mixture of three (o mega-l)-(2-hydroxyethylamino)alkanoic acids and of the corresponding a za-lactones were synthesized from (R)-alaninol. Gas chromatographic co mparison of MTPA-amides of the synthetic aza-lactones with the MTPA-am ides of aza-lactones prepared from the natural material established th at the polyazamacrolides have the (R)-configuration at all stereogenic centers. (C) 1998 Elsevier Science Ltd. All rights reserved.