Literature DB >> 12182619

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

Douglas B Weibel1, Laura E Shevy, Frank C Schroeder, Jerrold Meinwald.   

Abstract

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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Year:  2002        PMID： 12182619     DOI： 10.1021/jo011102q

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  2 in total

1.  Pinoresinol: A lignol of plant origin serving for defense in a caterpillar.

Authors:  Frank C Schroeder; Marta L del Campo; Jacqualine B Grant; Douglas B Weibel; Scott R Smedley; Kelly L Bolton; Jerrold Meinwald; Thomas Eisner
Journal:  Proc Natl Acad Sci U S A       Date:  2006-10-09       Impact factor: 11.205

2.  Synthesis of chemically edited derivatives of the endogenous regulator of inflammation 9-PAHSA.

Authors:  Huijing Wang; Tina Chang; Srihari Konduri; Jianbo Huang; Alan Saghatelian; Dionicio Siegel
Journal:  J Antibiot (Tokyo)       Date:  2019-04-15       Impact factor: 2.649
  2 in total

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