Tetrahedron Letters

Preparation of five-and six-membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis

J Tsuji, Y Kobayashi, H Kataoka, T Takahashi

Index: Tsuji, Jiro; Kobayashi, Yuichi; Kataoka, Hideaki; Takahashi, Takashi Tetrahedron Letters, 1980 , vol. 21, p. 1475 - 1478

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Citation Number: 105

Abstract

Abstract Methyl 3-oxo-8-phenoxy-6-octenoate (1) was cyclized using Pd (OAc) 2-PPh 3 as a catalyst to give 2-carbomethoxy-3-vinylcyclopentanone (2) and 2-carbomethoxy-4- cycloheptenone (3). The former was the main product in acetonitrile. 2-Alkylated 3-oxo-8- phenoxy-6-octenoates were converted mainly to the five-membered ketones. Based on this cyclization method, methyl dihydrojasmonate (8) was prepared from methyl 2-pentyl-3-oxo ...