When a beet armyworm caterpillar eats corn seedlings, it secretes volicitin onto the injured leaves. The leaves respond by releasing a volatile cocktail of terpenes and indoles that attract parasitic wasps, the natural enemies of the caterpillar. (For more details, read "New Fatty Acid-Based Signals: A Lesson from the Plant World" by E. E. Farmer in Science, May 9, 1997, p. 912.)

a. The amide volicitin is derived from a fatty acid and the amino acid glutamine (see Table 17.1). Which fatty
acid is present in volicitin? What is the configuration (Z or E) of each double bond?
b. What is the configuration (R or S) of the stereogenic center marked with an asterisk?

Transcribed Image Text:

OH HO dicitin