Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis
Publication type: Journal Article
Publication date: 1980-01-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
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).
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85
Total citations:
85
Citations from 2025:
1
(1.18%)
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GOST
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Tsuji J. et al. Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis // Tetrahedron Letters. 1980. Vol. 21. No. 15. pp. 1475-1478.
GOST all authors (up to 50)
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Tsuji J., Kobayashi Y., KATAOKA H., TAKAHASHI T. Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis // Tetrahedron Letters. 1980. Vol. 21. No. 15. pp. 1475-1478.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0040-4039(00)92750-3
UR - https://doi.org/10.1016/S0040-4039(00)92750-3
TI - Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis
T2 - Tetrahedron Letters
AU - Tsuji, Jiro
AU - Kobayashi, yuichi
AU - KATAOKA, Hideaki
AU - TAKAHASHI, Takashi
PY - 1980
DA - 1980/01/01
PB - Elsevier
SP - 1475-1478
IS - 15
VL - 21
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1980_Tsuji,
author = {Jiro Tsuji and yuichi Kobayashi and Hideaki KATAOKA and Takashi TAKAHASHI},
title = {Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis},
journal = {Tetrahedron Letters},
year = {1980},
volume = {21},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4039(00)92750-3},
number = {15},
pages = {1475--1478},
doi = {10.1016/S0040-4039(00)92750-3}
}
Cite this
MLA
Copy
Tsuji, Jiro, et al. “Preparation of five- and six- membered cyclic ketones by the palladium-catalyzed cyclization reaction. Application to methyl dihydrojasmonate synthesis.” Tetrahedron Letters, vol. 21, no. 15, Jan. 1980, pp. 1475-1478. https://doi.org/10.1016/S0040-4039(00)92750-3.