Literature DB >> 11804473

Total synthesis of ustiloxin D.

Bin Cao1, Haengsoon Park, Madeleine M Joullié.   

Abstract

The total synthesis of ustiloxin D, a highly potent inhibitor of microtubule assembly, has been achieved. Notable features are the use of nucleophilic aromatic substitution (SNAr) for the construction of a chiral tertiary alkyl-aryl ether linkage, Sharpless asymmetric aminohydroxylation for the formation of the beta-hydroxytyrosine moiety, macrolactamization, and regioselective methylation.

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Year:  2002        PMID: 11804473     DOI: 10.1021/ja017277z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  The enantioselective synthesis of phomopsin B.

Authors:  Joshua S Grimley; Andrew M Sawayama; Hiroko Tanaka; Michelle M Stohlmeyer; Thomas F Woiwode; Thomas J Wandless
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Structure-activity relationships of ustiloxin analogues.

Authors:  Madeleine M Joullié; Simon Berritt; Ernest Hamel
Journal:  Tetrahedron Lett       Date:  2011-04       Impact factor: 2.415

3.  Formation of Chiral Allylic Ethers via an Enantioselective Palladium-Catalyzed Alkenylation of Acyclic Enol Ethers.

Authors:  Harshkumar H Patel; Matthew B Prater; Scott O Squire; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2018-04-27       Impact factor: 15.419

4.  Total synthesis and configurational assignment of chondramide A.

Authors:  Anke Schmauder; L David Sibley; Martin E Maier
Journal:  Chemistry       Date:  2010-04-12       Impact factor: 5.236

5.  Evolution of the total syntheses of ustiloxin natural products and their analogues.

Authors:  Pixu Li; Cory D Evans; Yongzhong Wu; Bin Cao; Ernest Hamel; Madeleine M Joullié
Journal:  J Am Chem Soc       Date:  2008-01-30       Impact factor: 15.419

6.  Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes.

Authors:  David J Michaelis; Kevin S Williamson; Tehshik P Yoon
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

7.  Palladium-catalyzed allylic etherification of phenols with vinyl ethylene carbonate.

Authors:  Shibo Lin; Xiaotian Zhao; Lihui He; Xuanhao Li; Qian Jiang; Lan Xiang; Yongqin Ye; Xiaohong Gan
Journal:  Front Chem       Date:  2022-07-22       Impact factor: 5.545

  7 in total

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