Question 27.Int.1: The female of a species of worm produces the sex attractant ...
The female of a species of worm produces the sex attractant spodoptol, which has the following structure.
\begin{matrix} \ HO CH_2 CH_2 CH_2 CH_2 CH_2 CH_2 CH_2 CH_2\ _{_\diagdown }\quad\quad\ _{_\diagup }CH_2 CH_2 CH_2 CH_3 \quad\quad\quad\quad\quad\quad\quad\quad\quad\quad \ \\C=C\\ H\ ^{^\diagup }\quad \quad \ \ ^{^\diagdown }H \\ \\ \text{Spodoptol}\end{matrix}
Spodoptol is a pheromone that attracts the male worms of the species. Synthetic spodoptol in traps can be used to control the population of worms. Devise a synthesis of spodoptol starting from the alcohol shown below.
HO CH_2 CH_2 CH_2 CH_2 CH_2 CH_2 CH_2 CH_2 C \equiv CH
Analyze
In designing the synthesis, we break down the spodoptol molecule into the starting material and the necessary alkyl group that has to be attached to a double bond, namely a n-butyl group. In order to produce the alkene skeleton structure, we will have to convert the triple bond in the starting material to a double bond with cis stereochemistry.
