Synthesis of carbapenam skeletons using a ruthenium-catalyzed cyclization

被引：49

作者：

Mori, M ^{[1
]}

Kozawa, Y ^{[1
]}

Nishida, M ^{[1
]}

Kanamaru, M ^{[1
]}

Onozuka, K ^{[1
]}

Takimoto, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol006510f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Carbapenam is a very important skeleton of beta-lactam antibiotics, and it has a highly strained structure. When enynes 9 were treated with RuH2CO(PPh3)(3) (10 mol %) in toluene upon heating, carbapenams 10 were obtained in good yields.

引用

页码：3245 / 3247

页数：3

共 36 条

[1] APPLICATIONS OF ORGANOMETALLIC REAGENTS IN BETA-LACTAM CHEMISTRY
BARRETT, AGM
STURGESS, MA
[J]. TETRAHEDRON, 1988, 44 (18) : 5615 - 5652
[2] USE OF ORGANOIRON COMPLEXES IN BETA-LACTAM SYNTHESIS - PREPARATION OF 2-METHYLCARBOPENAM
BERRYHILL, SR
ROSENBLUM, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) : 1984 - 1986
[3] CYCLOPENTADIENYLRUTHENIUM PHOSPHINE COMPLEXES .2. REACTIONS BETWEEN HYDRIDOBIS(TRIPHENYLPHOSPHINE) (PI-CYCLOPENTADIENYL)RUTHENIUM AND ACETYLENES
BLACKMORE, T
BRUCE, MI
STONE, FGA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (01): : 106 - 112
[4] RUTHENIUM-CATALYZED REACTION OF 1,6-DIYNES WITH HYDROSILANES AND CARBON-MONOXIDE - A 3RD WAY OF INCORPORATING CO
CHATANI, N
FUKUMOTO, Y
MURAI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) : 11614 - 11615
[5] HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2)
CHATANI, N
MORIMOTO, T
MUTO, T
MURAI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) : 6049 - 6050
[6] Ru3(CO)12- and Rh4(CO)12-catalyzed reactions of pyridylolefins or N-(2-pyridyl)enamines with CO and olefins.: Carbonylation at olefinic C-H bonds
Chatani, N
Ishii, Y
Ie, Y
Kakiuchi, F
Murai, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) : 5129 - 5136
[7] Metal-catalyzed carbocyclization by intramolecular reaction of allylsilanes and allylstannanes with alkynes
Fernández-Rivas, C
Méndez, M
Echavarren, AM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) : 1221 - 1222
[8] Transition metal-catalyzed intramolecular C-H/olefin coupling
Fujii, N
Kakiuchi, F
Chatani, N
Murai, S
[J]. CHEMISTRY LETTERS, 1996, (11) : 939 - 940
[9] MECHANISTIC ASPECTS OF (C=C) ISOMERIZATION IN VINYLIC RHODIUM(III) COMPLEXES
HART, DW
SCHWARTZ, J
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 87 (01) : C11 - C14
[10] Chelation-assisted alkylation of benzylamine derivatives by Ru0 catalyst
Jun, CH
Hwang, DC
Na, SJ
[J]. CHEMICAL COMMUNICATIONS, 1998, (13) : 1405 - 1406

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