[3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 9. total synthesis of (±)-yellow scale pheromone via 10-membered thiolcarbonate

✍ Scribed by Shinya Harusawa; Shigetaka Takemura; Hirotaka Osaki; Ryuji Yoneda; Takushi Kurihara

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 770 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)87241-0

✦ Synopsis

Yellow scale pheromone 1 has been synthesized via the route illustrated in Scheme 1. The [3,3]sigmatropic ring expansion of I-membered thionocarbonate 4 exclusively produced the Q-lO-membered thiolcarbonate 3, which was transformed via three steps to the intermediate 2 with all the necessary carbon atoms for the pheromone. Reductive removal of the SC0 moiety in 2 followed by acetylation gave 1.