J. Tsuji*, Yuichi Kobayashi, H. Kataoka
1980
Citations
0
Influential Citations
72
Citations
Quality indicators
Journal
Tetrahedron Letters
Abstract
Abstract Methyl 3-oxo-8-phenoxy-6-octenoate ( 1 ) was cyclized using Pd(OAc)2-PPh3 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-8-phenoxy-6-octenoate ( 5 ). Methyl 3-oxo-9-phenoxy-7-nonenoate (10) was subjected to the palladium-catalyzed cyclization to afford 2-carbomethoxy-3-vinylcyclohexanone (11) selectively without forming the eight-membered ketone (12).