Synthesis of mayolene-16 and mayolene-18: larval defensive lipids from the European cabbage butterfly.
A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,12Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HLA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.
Weibel
Douglas B
DB
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
Shevy
Laura E
LE
Schroeder
Frank C
FC
Meinwald
Jerrold
J
D000818:Animals; D001681:Biological Assay; D002080:Butterflies / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D005231:Fatty Acids, Unsaturated / Q000032:analysis* / Q000138:chemical synthesis*; D007302:Insect Repellents / Q000032:analysis*; D007814:Larva / Q000187:drug effects; D008042:Linolenic Acids / Q000138:chemical synthesis*; D018942:Macrolides / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D005231:Fatty Acids, Unsaturated; D007302:Insect Repellents; D008042:Linolenic Acids; D018942:Macrolides; C456541:mayolene; C470898:mayolene-16; C470899:mayolene-18