As per what Jorriss indicates, I think the steps of conversion will involve the following -:
1. Addition of a halohydrin to the double bond(halohydrins are of the form X-OH where X is a halogen).
2. Oxidation of -OH to =O using Jones' reagent.
3. Favorskii reaction to prepare cyclopentanecarboxylic acid.
4. Hell-Volhardt-Zelinski reaction to alpha-brominate the carboxylic acid.
5. Strong base and high temperature to perform elimination, and avoid neighbouring group participation of -COOH as a carboxylate anion.