Highly Efficient Gold-Catalyzed Synthesis of Dibenzocycloheptatrienes

被引：36

作者：

Pflaesterer, Daniel ^{[1
]}

Rettenmeier, Eva ^{[1
]}

Schneider, Severin ^{[1
]}

Ruiz, Edgar de Las Heras ^{[1
]}

Rudolph, Matthias ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 22期

关键词：

dibenzocycloheptanoids; gold; hydroarylation; natural products; total synthesis; INTRAMOLECULAR ALKYNE HYDROARYLATION; C-H BONDS; CINNAMOMUM-SUBAVENIUM; HETEROARENES; DERIVATIVES; CYCLIZATION; COMPLEXES; CHEMISTRY; GOLD(III); TUBULIN;

D O I：

10.1002/chem.201402015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dibenzocycloheptatrienes are obtained by a gold-catalyzed 7-exo-dig hydroarylation protocol in a highly efficient manner. The gold-catalyzed reaction usually gives the products in high yields and excellent selectivity. This procedure provides an easy and efficient access to dibenzocycloheptanoids, which are an interesting and unique class of natural products. This was underlined by the first total synthesis of reticuol.

引用

页码：6752 / 6755

页数：4

共 50 条

[41] Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers
Boreux, Arnaud
Lonca, Geoffroy H.
Riant, Olivier
Gagosz, Fabien
[J]. ORGANIC LETTERS, 2016, 18 (19) : 5162 - 5165
[42] Atroposelective Synthesis of Axially Chiral All-Benzenoid Biaryls by the Gold-Catalyzed Intramolecular Hydroarylation of Alkynones
Satoh, Masakazu
Shibata, Yu
Kimura, Yuki
Tanaka, Ken
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (26) : 4465 - 4469
[43] Protecting-Group-Free Total Synthesis of (-)-Rhazinilam and (-)-Rhazinicine using a Gold-Catalyzed Cascade Cyclization
Sugimoto, Kenji
Toyoshima, Kazuki
Nonaka, Shiori
Kotaki, Kenta
Ueda, Hirofumi
Tokuyama, Hidetoshi
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7168 - 7171
[44] An Efficient Method for the Synthesis of Alkylidenecyclobutanones by Gold-Catalyzed Oxidative Ring Enlargement of Vinylidenecyclopropanes
Yuan, Wei
Dong, Xiang
Wei, Yin
Shi, Min
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (34) : 10501 - 10505
[45] New pathways in the gold-catalyzed cycloisomerization of furanynes
Hashmi, A. Stephen K.
[J]. PURE AND APPLIED CHEMISTRY, 2010, 82 (07) : 1517 - 1528
[46] Intermolecular Gold-Catalyzed Cycloaddition of Alkynes with Oxoalkenes
Obradors, Carla
Echavarren, Antonio M.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (11) : 3547 - 3551
[47] Gold-Catalyzed Enantioselective Annulations
Li, Yangyan
Li, Wenbo
Zhang, Junliang
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (03) : 467 - 512
[48] Gold-catalyzed Dearomatization Reactions
An, Juzeng
Bandini, Marco
[J]. CHIMIA, 2018, 72 (09) : 610 - 613
[49] Gold-catalyzed multicomponent reactions
Tathe, Akash. G. G.
Saswade, Sagar. S. S.
Patil, Nitin. T. T.
[J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (09) : 2359 - 2384
[50] Highly Efficient and Tunable Synthesis of Dioxabicyclo[4.2.1] Ketals and Tetrahydropyrans via Gold-Catalyzed Cycloisomerization of 2-Alkynyl-1,5-diols
Liu, Le-Ping
Hammond, Gerald B.
[J]. ORGANIC LETTERS, 2009, 11 (21) : 5090 - 5092

← 1 2 3 4 5 →