Ruthenium-Catalyzed Cycloisomerization and Its Application to the Synthesis of (±)-Cinchonaminone

被引：10

作者：

Ogawa, Takao ^{[1
]}

Nakamura, Tomonori ^{[2
]}

Araki, Takuya ^{[2
]}

Yamamoto, Koujirou ^{[2
]}

Shuto, Satoshi ^{[1
]}

Arisawa, Mitsuhiro ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Gunma Univ, Dept Clin Pharmacol, Grad Sch Med, Maebashi, Gunma 3718511, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 16期

关键词：

Heterocycles; Cyclization; Ruthenium; Natural products; Total synthesis; INDOLES; CARBOCYCLIZATIONS; CARBENE; ISOMERIZATION; REARRANGEMENT;

D O I：

10.1002/ejoc.201200260

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (+/-)-cinchonaminone.

引用

页码：3084 / 3087

页数：4

共 50 条

[21] Ruthenium-catalyzed cycloisomerization of 1,6-enynes initiated by C-H activation
Trost, BM
Toste, FD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9728 - 9729
[22] Palladium- and Ruthenium-Catalyzed Cycloisomerization of Enynamides and Enynhydrazides: A Rapid Approach to Diverse Azacyclic Frameworks
Walker, P. Ross
Campbell, Craig D.
Suleman, Abid
Carr, Greg
Anderson, Edward A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9139 - 9143
[23] Ruthenium-Catalyzed Cycloisomerization of 1,6-Diynes with Styryl Terminals Leading to Indenylidene Cycloalkanes
Yamamoto, Yoshihiko
Nishimura, Kei-ichiro
Shibuya, Masatoshi
ACS CATALYSIS, 2017, 7 (02): : 1101 - 1107
[24] Ruthenium-Catalyzed Synthesis of β-Hydroxyamides from β-Ketonitriles in Water
Gonzalez-Fernandez, Rebeca
Crochet, Pascale
Cadierno, Victorio
ORGANIC LETTERS, 2016, 18 (23) : 6164 - 6167
[25] Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
Semina, Elena
Tuzina, Pavel
Bienewald, Frank
Hashmi, A. Stephen K.
Schaub, Thomas
CHEMICAL COMMUNICATIONS, 2020, 56 (44) : 5977 - 5980
[26] Ruthenium-Catalyzed Isomerization of Terminal Olefins: Applications to Synthesis
Donohoe, Timothy J.
O'Riordan, Timothy J. C.
Rosa, Carla P.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (06) : 1014 - 1017
[27] Ruthenium-catalyzed synthesis of α-deuterated polyols for hyperpolarized imaging
Sail, Deepak
Opina, Ana Christina
Vasalatiy, Olga
Mitchell, James
Krishna, Murali
Swenson, Rolf
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[28] Synthesis of carbapenam skeletons using a ruthenium-catalyzed cyclization
Mori, M
Kozawa, Y
Nishida, M
Kanamaru, M
Onozuka, K
Takimoto, M
ORGANIC LETTERS, 2000, 2 (20) : 3245 - 3247
[29] Ruthenium-Catalyzed Synthesis of Indoles from Anilines and Epoxides
Pena-Lopez, Miguel
Neumann, Helfried
Beller, Matthias
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (07) : 1818 - 1824
[30] RUTHENIUM-CATALYZED SYNTHESIS OF 1-SUBSTITUTED PERHYDROAZEPINES
SHIM, SC
DOH, CH
WOO, BW
KIM, HS
HUH, KT
PARK, WH
LEE, H
JOURNAL OF MOLECULAR CATALYSIS, 1990, 62 (02): : L11 - L15

← 1 2 3 4 5 →