Synthesis of mayolene-16 and mayolene-18: larval defensive lipids from the European cabbage butterfly.

نویسندگان

  • Douglas B Weibel
  • Laura E Shevy
  • Frank C Schroeder
  • Jerrold Meinwald
چکیده

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.

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عنوان ژورنال:
  • The Journal of organic chemistry

دوره 67 17  شماره 

صفحات  -

تاریخ انتشار 2002