Chemoselective and Diastereoconvergent Cu(II)-Catalyzed Aerobic Endoperoxidation of Polycarbonyls

被引：11

作者：

Giarrusso, James ^{[1
]}

Do, Dung T. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ North Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 12期

基金：

美国国家科学基金会;

关键词：

ALPHA-KETO ESTERS; ORGANIC PEROXIDES; BETA-KETOESTERS; OXYGEN; HYDROGENATION; ARTEMISININ; OXIDATION; PRODUCTS; IONS;

D O I：

10.1021/acs.orglett.7b01225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoconvergent synthesis of spirocyclic endoperoxides using a Meldrum's acid scaffold has been accomplished by employing readily available feedstock Chemicals. Site selective C-H oxidation of the bis(beta-dicarbonyl) substrates was performed using, elemental oxygen as the stoichiometric oxidant and a commercial Cu(II) catalyst. Sequential hydrogenolysis and ionic reduction of these-endoperoxides provided fully substituted tetrahydrofurans in high-yields and diastereoselectivity.

引用

收藏

页码：3107 / 3110

页数：4

相关论文

共 31 条

[1] Natural Endoperoxides as Drug Lead Compounds [J].

Bu, Ming ;

Yang, Burton B. ;

Hu, Liming .

CURRENT MEDICINAL CHEMISTRY, 2016, 23 (04) :383-405

[2] Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].

Campbell, Alison N. ;

Stahl, Shannon S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863

[3] Formation of an Endoperoxide upon Chromium-Catalyzed Allylic Oxidation of a Triterpene by Oxygen [J].

Chung, Abbie ;

Miner, Matthew R. ;

Richert, Kathleen J. ;

Rieder, Curtis J. ;

Woerpel, K. A. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :266-273

[4] OXIDATIVE CLEAVAGE OF 2-SUBSTITUTED CYCLOALKANE-1,3-DIONES AND OF CYCLIC BETA-KETOESTERS BY COPPER PERCHLORATE/OXYGEN [J].

COSSY, J ;

BELOTTI, D ;

BELLOSTA, V ;

BROCCA, D .

TETRAHEDRON LETTERS, 1994, 35 (33) :6089-6092

[5] Bioactive peroxides as potential therapeutic agents [J].

Dembitsky, Valery M. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) :223-251

[6] Hazard ratings for organic peroxides [J].

Duh, Yih-Shing ;

wu, Xiao Hui ;

Kao, Chen-Shan .

PROCESS SAFETY PROGRESS, 2008, 27 (02) :89-99

[7] FACILE ACCESS TO 3-ALKYL-SUBSTITUTED 3-HYDROPEROXY-2,4-PYRROLIDINEDIONES USING MANGANESE(III)-CATALYZED AEROBIC OXIDATION [J].

Haque, M. Aminul ;

Nishino, Hiroshi .

SYNTHETIC COMMUNICATIONS, 2012, 42 (04) :608-619

[8] Two-Phase Terpene Total Synthesis: Historical Perspective and Application to the Taxol® Problem [J].

Ishihara, Yoshihiro ;

Baran, Phil S. .

SYNLETT, 2010, (12) :1733-1745

[9] Electrophilicity parameters of 5-benzylidene-2,2-dimethyl[1,3]dioxane-4,6-diones (benzylidene Meldrum's acids) [J].

Kaumanns, Oliver ;

Mayr, Herbert .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2738-2745

[10] ISOLATION OF ARTEMISININ [QINGHAOSU) FROM ARTEMISIA-ANNUA GROWING IN THE UNITED-STATES [J].

KLAYMAN, DL ;

LIN, AJ ;

ACTON, N ;

SCOVILL, JP ;

HOCH, JM ;

MILHOUS, WK ;

THEOHARIDES, AD .

JOURNAL OF NATURAL PRODUCTS, 1984, 47 (04) :715-717

← 1 2 3 4 →