142011-66-3Relevant academic research and scientific papers
SIGMATROPIC RING EXPANSION OF CYCLIC THIONOCARBONATES. 9. TOTAL SYNTHESIS OF (+/-)-YELLOW SCALE PHEROMONE VIA 10-MEMBERED THIOLCARBONATE
Harusawa, Shinya,Takemura, Shigetaka,Osaki, Hirotaka,Yoneda, Ryuji,Kurihara, Takushi
, p. 7657 - 7666 (2007/10/02)
(+/-)-Yellow scale pheromone 1 has been synthesized via the route illustrated in Scheme 1.The sigmatropic ring expansion of 8-membered thionocarbonate 4 exclusively produced the (Z)-10-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 SCO mioety in 2 followed by acetylation gave 1.
