Synthesis of the three isomeric components of San Jose scale pheromone

✍ Scribed by Margot Alderdice; Claude Spino; Larry Weiler

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 199 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81133-3

✦ Synopsis

The three isomeric components of the San Jose scale pheromone have been synthesized stereospecifically from a common intermediate S-keto ester. which fruit Three (1).

The San Jose scale, Quadraspidiotus pernicious, is a serious world-wide insect pest attacks fruit, shade, and ornamental trees. It is particularly harmful to deciduous trees, and for this reason it is a serious economic pest in North Ameritan orchards.

active components, l-3, have been isolated from the pheromone mixture of female scales NN Al1 three components were found to be almost equally attractive to male scales (1). In this paper, we report a stereospecific synthesis of each of the isomers of the pheromone from a common precursor.

*OCOE+

I '-ocoE+ 2 3

Recently, we have developed a stereoselective method to convert a S-keto ester into the alkene 4, as shown in equation 1 (2). We now report methods to convert this same S-keto ester into the alkene 2 and the l,l-disubstituted alkene 6.