Second-Generation Total Synthesis of Spirastrellolide F Methyl Ester: The Alkyne Route

被引：100
作者：
Benson, Stefan [1 ]
Collin, Marie-Pierre [1 ]
Arlt, Alexander [1 ]
Gabor, Barbara [1 ]
Goddard, Richard [1 ]
Fuerstner, Alois [1 ]
机构：
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 37期
关键词：
alkyne metathesis; gold; molybdenum; natural products; total synthesis; ANTI-MARKOVNIKOV HYDRATION; CONCISE TOTAL-SYNTHESIS; ANION RELAY CHEMISTRY; DEF-BIS-SPIROACETAL; TERMINAL ALKYNES; PART; STEREOCHEMICAL ASSIGNMENT; STEREOSELECTIVE-SYNTHESIS; STRATEGIC CONSIDERATIONS; METATHESIS CATALYSTS;
D O I：
10.1002/anie.201103270
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Outlandish: The spiroketal embedded in spirastrellolide F methyl ester is a daring site for ring closure, yet it has allowed the power of catalytic alkyne scission and activation to be showcased (see scheme). An improved strategy for the introduction of the labile side chain was also developed. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8739 / 8744
页数：6
相关论文
共 102 条
[1]   Gold catalyzed oxycyclizations of alkynols and alkyndiols [J].
Alcaide, Benito ;
Almendros, Pedro ;
Miguel Alonso, Jose .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4405-4416
[2]  
[Anonymous], 2007, ANGEW CHEM
[3]  
[Anonymous], 2001, ANGEW
[4]  
[Anonymous], 2005, ANGEW CHEM
[5]   Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals [J].
Aponick, Aaron ;
Li, Chuan-Ying ;
Palmes, Jean A. .
ORGANIC LETTERS, 2009, 11 (01) :121-124
[6]  
Benson S., 2009, ANGEW CHEM, V121, p10130 10134
[7]   Total Synthesis of Spirastrellolide F Methyl Ester-Part 2: Macrocyclization and Completion of the Synthesis [J].
Benson, Stefan ;
Collin, Marie-Pierre ;
O'Neil, Gregory W. ;
Ceccon, Julien ;
Fasching, Bernhard ;
Fenster, Michael D. B. ;
Godbout, Cedrickx ;
Radkowski, Karin ;
Goddard, Richard ;
Fuerstner, Alois .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9946-9950
[8]   Inhibitors of protein tyrosine phosphatases: Next-generation drugs? [J].
Bialy, L ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3814-3839
[9]  
Bialy L., 2005, ANGEW CHEM, V117, P3880, DOI DOI 10.1002/ANGE.200461517
[10]  
Blakemore PR, 1998, SYNLETT, P26
12345678910