Literature DB >> 19378315

A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.

Paul M Wehn1, J Du Bois.   

Abstract

Weaving an intricate web: A stereoselective synthesis of (-)-agelastatin A has been developed, which requires 11 steps from commercially available starting material. The application of a Rh-catalyzed intramolecular olefin aziridination reaction and the subsequent manipulation of the resulting tricyclic intermediate (see scheme) punctuate this study.

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Year:  2009        PMID： 19378315      PMCID： PMC2791535          DOI： 10.1002/anie.200806292

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  41 in total

1.  Novel screening methods--the key to cloning commercially successful biocatalysts.

Authors:  S J Taylor; R C Brown; P A Keene; I N Taylor
Journal:  Bioorg Med Chem       Date:  1999-10       Impact factor: 3.641

2.  Rhodium(II,II) dimer as an efficient catalyst for aziridination of sulfonamides and amidation of steroids.

Authors:  Jiang-Lin Liang; Shi-Xue Yuan; Philip Wai Hong Chan; Chi-Ming Che
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

3.  Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.

Authors:  Karl J Hale; Mathias M Domostoj; Derek A Tocher; Ed Irving; Feodor Scheinmann
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

4.  A stereoselective synthesis of (-)-tetrodotoxin.

Authors:  Andrew Hinman; J Du Bois
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

5.  Enantioselective synthesis of the bromopyrrole alkaloids manzacidin A and C by stereospecific C-h bond oxidation.

Authors:  Paul M Wehn; J Du Bois
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

6.  Organic azides: an exploding diversity of a unique class of compounds.

Authors:  Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

7.  Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B.

Authors:  Ken S Feldman; Joe C Saunders; Michelle Laci Wrobleski
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354

8.  Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines.

Authors:  John F Bower; Peter Szeto; Timothy Gallagher
Journal:  Org Lett       Date:  2007-10-20       Impact factor: 6.005

9.  Intramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: amidation of sulfamate esters and aziridination of unsaturated sulfonamides.

Authors:  Jiang-Lin Liang; Shi-Xue Yuan; Jie-Sheng Huang; Chi-Ming Che
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

10.  Callipeltoside a: total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues.

Authors:  Barry M Trost; Janet L Gunzner; Olivier Dirat; Young H Rhee
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  16 in total

1.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

2.  Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.

Authors:  Alyssa H Antropow; Kun Xu; Rachel J Buchsbaum; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2017-07-25       Impact factor: 4.354

3.  Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors:  Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-14       Impact factor: 15.336

4.  Preparation of bifunctional isocyanate hydroxamate linkers: Synthesis of carbamate and urea tethered polyhydroxamic acid chelators.

Authors:  Rasika Fernando; Jonathan M Shirley; Emilio Torres; Hollie K Jacobs; Aravamudan S Gopalan
Journal:  Tetrahedron Lett       Date:  2012-11-21       Impact factor: 2.415

5.  Bioinspired total synthesis of agelastatin A.

Authors:  Jeremy Chris P Reyes; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-11       Impact factor: 15.336

6.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

7.  Total synthesis of all (-)-Agelastatin alkaloids.

Authors:  Mohammad Movassaghi; Dustin S Siegel; Sunkyu Han
Journal:  Chem Sci       Date:  2010-01-01       Impact factor: 9.825

8.  Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

Authors:  Jennifer L Roizen; Mark Edwin Harvey; J Du Bois
Journal:  Acc Chem Res       Date:  2012-04-30       Impact factor: 22.384

9.  Derivatization of agelastatin A leading to bioactive analogs and a trifunctional probe.

Authors:  Morgan Jouanneau; Brandon McClary; Jeremy Chris P Reyes; Rong Chen; Yuling Chen; William Plunkett; Xin Cheng; Andrew Z Milinichik; Earl F Albone; Jun O Liu; Daniel Romo
Journal:  Bioorg Med Chem Lett       Date:  2016-02-23       Impact factor: 2.823

Review 10.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118
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