Palladium(0)-catalyzed [2+2+1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers

被引：3

作者：

Diao, Yunxia ^{[1
]}

Zuo, Zhijun ^{[1
]}

Wang, Hui ^{[1
]}

Liu, Jingjing ^{[1
]}

Luan, Xinjun ^{[1
]}

机构：

[1] Northwest Univ, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Coll Chem & Mat Sci, Xian 710127, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 21期

关键词：

PAUSON-KHAND REACTION; ASYMMETRIC-SYNTHESIS; ANISLACTONE-B; RHODIUM; CYCLOADDITION; ENYNES; RING; CARBOCYCLIZATION; MERRILACTONE; FUSARISETIN;

D O I：

10.1039/c7ob00768j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides. Notably, the key feature of this transformation is the use of vinyl bromides as the C1 building block. Various functionalized tetrahydro-1H-cyclopenta[c] furans bearing two quaternary carbon centers could be obtained in good yields with excellent diastereoselectivities.

引用

页码：4601 / 4608

页数：8

共 71 条

[1] Ceriopsin E, a new epoxy ent-kaurene diterpenoid from Ceriops decandra [J].

Anjaneyulu, ASR ;

Rao, VL ;

Lobkovsky, E ;

Clardy, J .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (04) :592-594

[2] Microbial Transformations of the Taxan Ring of 10-DAB by Some Strains of the Fungus Curvularia lunata: Formation of the Bis-abeotaxanes Wallifoliol and 4-Deacylwallifoliol [J].

Arnone, Alberto ;

Bava, Adriana ;

Fronza, Giovanni ;

Malpezzi, Luciana ;

Nasini, Gianluca .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (06) :1049-1052

[3] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[4]

Aubert C, 2006, TOP ORGANOMETAL CHEM, V19, P259

[5] Palladium(0)-Catalyzed Intermolecular Carbocyclization of (1,n)-Diynes and Bromophenols: An Efficient Route to Tricyclic Scaffolds [J].

Bai, Lu ;

Yuan, Yini ;

Liu, Jingjing ;

Wu, Jiaoyu ;

Han, Lingbo ;

Wang, Hui ;

Wang, Yaoyu ;

Luan, Xinjun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (24) :6946-6950

[6] Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate [J].

Bardsley, Ben ;

Smith, Marco S. ;

Gibbon, Bob H. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (08) :1876-1880

[7] The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules [J].

Blanco-Urgoiti, J ;

Añorbe, L ;

Pérez-Serrano, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :32-42

[8] CYCLO-ADDITIONS OF 1-(4-METHOXYPHENYL)-2-METHYLVINYL CATION TO OLEFINS - STEREOCHEMISTRY AND STRUCTURE OF THE REACTION-PRODUCTS [J].

BOFINGER, KR ;

HANACK, M .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (07) :2993-3003

[9] PALLADIUM CATALYZED [2+2+2]-CYCLOADDITION REACTIONS VIA CARBOPALLADATION OF 1,6-ENYNES [J].

BROWN, S ;

CLARKSON, S ;

GRIGG, R ;

SRIDHARAN, V .

TETRAHEDRON LETTERS, 1993, 34 (01) :157-160

[10] Oxetanes as Versatile Elements in Drug Discovery and Synthesis [J].

Burkhard, Johannes A. ;

Wuitschik, Georg ;

Rogers-Evans, Mark ;

Mueller, Klaus ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) :9052-9067

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