Concise Total Synthesis of (-)-Myxalamide A

被引：41

作者：

Fujita, Kazuhiro ^{[1
]}

Matsui, Ryosuke ^{[1
]}

Suzuki, Takahiro ^{[1
]}

Kobayashi, Susumu ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Noda, Chiba 2788510, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 29期

关键词：

aldol reaction; cross-coupling; polyene antibiotics; protecting-group-free synthesis; total synthesis; 1ST TOTAL-SYNTHESIS; MUKAIYAMA ALDOL REACTION; ELECTRON-TRANSPORT INHIBITORS; MULTIDRUG-RESISTANCE REVERSAL; INDEXED COMBINATORIAL LIBRARY; BIOACTIVE NATURAL-PRODUCTS; SMALL-MOLECULE SYNTHESIS; STRUCTURAL DETERMINATION; GLIDING BACTERIA; NONNATURAL POLYENES;

D O I：

10.1002/anie.201203093

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The MIDA touch: A concise and highly convergent protecting-group-free total synthesis of (-)-myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O-acetal, together with a one-pot Stille/Suzuki-Miyaura cross-coupling reaction using Burke's N- methyliminodiacetic acid (MIDA) boronate to connect left- and right-hand fragments of the molecule (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7271 / 7274

页数：4

共 62 条

[1] The synthesis and evaluation of a solution phase indexed combinatorial library of non-natural polyenes for reversal of p-glycoprotein mediated multidrug resistance [J].

Andrus, MB ;

Turner, TM ;

Sauna, ZE ;

Ambudkar, SV .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4973-4983

[2] The synthesis and evaluation of a solution-phase indexed combinatorial library of non-natural polyenes for multidrug resistance reversal [J].

Andrus, MB ;

Turner, TM ;

Asgari, D ;

Li, WK .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :2978-2979

[3] Synthesis of stipiamide and a new multidrug resistance reversal agent, 6,7-dehydrostipiamide [J].

Andrus, MB ;

Lepore, SD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2327-2328

[4] Total synthesis of stipiamide and designed polyenes as new agents for the reversal of multidrug resistance [J].

Andrus, MB ;

Lepore, SD ;

Turner, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12159-12169

[5]

[Anonymous], 2011, ANGEW CHEM-GER EDIT

[6] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[7] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress [J].

Casiraghi, Giovanni ;

Battistini, Lucia ;

Curti, Claudio ;

Rassu, Gloria ;

Zanardi, Franca .

CHEMICAL REVIEWS, 2011, 111 (05) :3076-3154

[8] Total synthesis of 2′-O-methylmyxalamide D and (6E)-2′-O-methylmyxalamide D [J].

Coleman, Robert S. ;

Lu, Xiaoling ;

Modolo, Isabelle .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3826-+

[9] SYNTHETIC STUDIES ON ELECTRON-TRANSPORT INHIBITORS .1. CHIRAL SYNTHESIS OF A SYNTHON FOR MYXALAMIDE-D, PIERICIDIN-A, AND THE ACTINOPYRONES [J].

COX, CM ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08) :1901-1905

[10] SYNTHETIC STUDIES ON ELECTRON-TRANSPORT INHIBITORS .2. APPROACHES TO THE SYNTHESIS OF MYXALAMIDE-D [J].

COX, CM ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08) :1907-1911

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