Synthesis of cis-Octahydroindoles via Intramolecular 1,3-Dipolar Cycloaddition of 2-Acyl-5-aminooxazolium Salts

被引：9

作者：

Basch, Corey H. ^{[1
]}

Brinck, Jameson A. ^{[1
]}

Ramos, Joaquin E. ^{[1
]}

Habay, Stephen A. ^{[1
]}

Yap, Glenn Pa ^{[2
]}

机构：

[1] Salisbury Univ, Henson Sch Sci & Technol, Dept Chem, Salisbury, MD 21801 USA

[2] Univ Delaware, Dept Chem & Biochem, Brown Lab 236, Newark, DE 19716 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 22期

基金：

美国国家科学基金会;

关键词：

AZOMETHINE YLIDES; ENANTIOSELECTIVE SYNTHESIS; AMINO-ACID; AERUGINOSINS; ALKYNES;

D O I：

10.1021/jo301600p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise method for the diastereoselective synthesis of octahydroindoles is presented. The products contain 2-amido and 7-hydroxyl substituents. A series of 2-acyl-5-aminooxazoles were prepared in one step. Upon methylation of the oxazole nitrogen atom, the substrates underwent rapid intramolecular 1,3-dipolar cycloaddition with a tethered alkene and, after reduction with excess hydride, produced octahydroindoles with excellent diastereoselectivity. The method allows for the installation of a-quaternary stereogenic carbon atoms.

引用

页码：10416 / 10421

页数：6

共 30 条

[1]

Ahmed M. G., 1980, J CHEM SOC PERK T, V1, P2383

[2] A concise asymmetric synthesis of the ADE fragment of nakadomarin [J].

Ahrendt, KA ;

Williams, RM .

ORGANIC LETTERS, 2004, 6 (24) :4539-4541

[3] Synthesis of the octahydroindole core of aeruginosins: A new bicyclic alpha-amino acid [J].

Bonjoch, J ;

Catena, J ;

Isabal, E ;

LopezCanet, M ;

Valls, N .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1899-1902

[4]

Burrell AJM, 2010, CURR ORG SYNTH, V7, P312

[5] Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].

Coldham, I ;

Hufton, R .

CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809

[6]

Coldham I., 2001, J CHEM SOC P1, VI, P1758

[7] Parallel synthesis of arrays of amino-acid-derived isocyanoamides useful as starting materials in IMCR [J].

Doemling, Alexander ;

Beck, Barbara ;

Fuchs, Thilo ;

Yazbak, Ahmad .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (06) :872-880

[8] Highly Efficient Narasaka-Heck Cyclizations Mediated by P(3,5-(CF3)2C6H3)3: Facile Access to N-Heterobicyclic Scaffolds [J].

Faulkner, Adele ;

Bower, John F. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1675-1679

[9] TOTAL SYNTHESIS OF GLIOTOXIN [J].

FUKUYAMA, T ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6723-6724

[10] Synthesis of Unsymmetrical 3,4-Diaryl-3-pyrrolin-2-ones Utilizing Pyrrole Weinreb Amides [J].

Greger, Jessica G. ;

Yoon-Miller, Sarah J. P. ;

Bechtold, Nathan R. ;

Flewelling, Scott A. ;

MacDonald, Jacob P. ;

Downey, Catherine R. ;

Cohen, Eric A. ;

Pelkey, Erin T. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (20) :8203-8214

← 1 2 3 →