Total Synthesis of Ustiloxin D Utilizing an Ammonia-Ugi Reaction

被引：23

作者：

Brown, Aaron L.

Churches, Quentin I.

Hutton, Craig A. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

基金：

澳大利亚研究理事会;

关键词：

FALSE SMUT BALLS; MULTICOMPONENT REACTIONS; NATURAL-PRODUCTS; 4-COMPONENT; SELECTIVITY;

D O I：

10.1021/acs.joc.5b01519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of the highly functionalized cyclic peptide natural product, ustiloxin D, has been achieved in a convergent manner. Our strategy incorporates an asymmetric allylic alkylation to construct the tert-alkyl aryl ether linkage between the dopa and isoleucine residues. The elaborated beta-hydroxydopa derivative is rapidly converted to a linear tripeptide through an ammonia-Ugi reaction. Subsequent cyclization and global deprotection affords ustiloxin D in six steps from a known beta-hydroxydopa derivative.

引用

收藏

页码：9831 / 9837

页数：7

相关论文

共 31 条

[21] INTERACTION OF USTILOXIN-A WITH BOVINE BRAIN TUBULIN [J].

LUDUENA, RF ;

ROACH, MC ;

PRASAD, V ;

BANERJEE, M ;

KOISO, Y ;

LI, Y ;

IWASAKI, S .

BIOCHEMICAL PHARMACOLOGY, 1994, 47 (09) :1593-1599

[22] Synthesis and anti-tubulin activity of Ustiloxin D derivatives [J].

Morisaki, N ;

Mitsui, Y ;

Yamashita, Y ;

Koiso, Y ;

Shirai, R ;

Hashimoto, Y ;

Iwasaki, S .

JOURNAL OF ANTIBIOTICS, 1998, 51 (04) :423-427

[23] Ammonia in Ugi reactions - Four-component versus six-component couplings [J].

Pick, R ;

Bauer, M ;

Kazmaier, U ;

Hebach, C .

SYNLETT, 2005, (05) :757-760

[24] Asymmetric multicomponent reactions (AMCRs):: The new frontier [J].

Ramón, DJ ;

Yus, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1602-1634

[25] Total synthesis of ustiloxin D and considerations on the origin of selectivity of the asymmetric allylic alkylation [J].

Sawayama, AM ;

Tanaka, H ;

Wandless, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8810-8820

[26] Enantioselective total synthesis of ustiloxin D [J].

Tanaka, H ;

Sawayama, AM ;

Wandless, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (23) :6864-6865

[27] Versatile assembly of 5-aminothiazoles based on the Ugi four-component coupling [J].

Thompson, Mark J. ;

Chen, Beining .

TETRAHEDRON LETTERS, 2008, 49 (36) :5324-5327

[28] Cyclic 1,2-Diketones as Core Building Blocks: A Strategy for the Total Synthesis of (-)-Terpestacin [J].

Trost, Barry M. ;

Dong, Guangbin ;

Vance, Jennifer A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (21) :6265-6277

[29] The chemistry of isocyanides, their multicomponent reactions and their libraries [J].

Ugi, I ;

Werner, B ;

Dömling, A .

MOLECULES, 2003, 8 (01) :53-66

[30] Recent Advances in Asymmetric Isocyanide-Based Multicomponent Reactions [J].

van Berkel, Sander S. ;

Bogels, Berry G. M. ;

Wijdeven, Marloes A. ;

Westermann, Bernhard ;

Rutjes, Floris P. J. T. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) :3543-3559

← 1 2 3 4 →