We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Synthesis of Four Stereoisomers of ( S)-2-Methylpent-3-yl 3,13-Dimethylpentadecanoate, a Sex Pheromone of the Bagworm Moth Clania variegate, Using Stereospecific Inversion of Secondary Sulfonates as a Key Step.
- Authors
Taguri, Tomonori; Yamamoto, Masanobu; Fujii, Toru; Muraki, Yuta; Ando, Tetsu
- Abstract
Females of some lepidopteran species produce novel sex pheromones with a methyl-branched structure, such as 2-methylpent-3-yl 3,13-dimethylpentadecanoate secreted by the bagworm moth Clania variegate. Recently, we have established a simple preparative method for the synthesis of methyl-branched building blocks by utilizing an SN2 reaction of chiral secondary tosylates derived from ( S)- and ( R)-propylene oxides. The usefulness of these building blocks was demonstrated by their application in the synthesis of all four stereoisomers of an acid moiety in the bagworm pheromone. The enantiomeric purities of all building blocks were confirmed by enantioselective HPLC analysis. We found that a secondary mesylate was superior to the corresponding tosylate because it avoided an elimination side reaction, and racemization in the SN2 reaction was not observed even at high temperature (150 °C). Finally, each optically active acid was esterified with ( S)-2-methyl-3-pentanol, which was synthesized by a new route starting from ( S)-valine.
- Subjects
CHEMICAL synthesis; STEREOISOMERS; PHEROMONES; PSYCHIDAE; ENANTIOMERS; HIGH performance liquid chromatography; METHANESULFONATES
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 30, p6924
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300874