Tetrahedron

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

S Harusawa, S Takemura, H Osaki, R Yoneda…

Index: Harusawa, Shinya; Takemura, Shigetaka; Osaki, Hirotaka; Yoneda, Ryuji; Kurihara, Takushi Tetrahedron, 1993 , vol. 49, # 35 p. 7657 - 7666

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Citation Number: 11

Abstract

(±)-Yellow scale pheromone 1 has been synthesized via the route illustrated in Scheme 1. The [3, 3] 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 moiety in 2 followed by acetylation gave 1.