Literature DB >> 10649416

Total Synthesis of the Antimicrotubule Agent (+)-Discodermolide Using Boron-Mediated Aldol Reactions of Chiral Ketones.

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Abstract

With a similar mechanism of action to taxol, the title compound 1 is a particularly promising candidate for development in cancer chemotherapy. This efficient synthesis, based on stereocontrolled aldol reactions, should help to overcome the scarce natural supply of 1 from the rare sponge source.

Entities:  

Year:  2000        PMID： 10649416     DOI： 10.1002/(sici)1521-3773(20000117)39:2<377::aid-anie377>3.0.co;2-e

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


  12 in total

1.  (+)-Discodermolide: Total Synthesis, Construction of Novel Analogues, and Biological Evaluation.

Authors:  Amos B Smith; B Scott Freeze
Journal:  Tetrahedron       Date:  2007-01-07       Impact factor: 2.457

2.  Induction of accelerated senescence by the microtubule-stabilizing agent peloruside A.

Authors:  Ariane Chan; Connie Gilfillan; Nikki Templeton; Ian Paterson; Peter T Northcote; John H Miller
Journal:  Invest New Drugs       Date:  2017-07-22       Impact factor: 3.850

Review 3.  Advances in exploring the therapeutic potential of marine natural products.

Authors:  Xiao Liang; Danmeng Luo; Hendrik Luesch
Journal:  Pharmacol Res       Date:  2019-07-25       Impact factor: 7.658

Review 4.  Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

Authors:  Jeffrey S Cannon; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

5.  The quest for supernatural products: the impact of total synthesis in complex natural products medicinal chemistry.

Authors:  Zhi-Chen Wu; Dale L Boger
Journal:  Nat Prod Rep       Date:  2020-11-10       Impact factor: 13.423

Review 6.  Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

Authors:  Carlo Ballatore; Kurt R Brunden; Donna M Huryn; John Q Trojanowski; Virginia M-Y Lee; Amos B Smith
Journal:  J Med Chem       Date:  2012-09-28       Impact factor: 7.446

7.  Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.

Authors:  Zhiyong Yu; Robert J Ely; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

8.  Total synthesis and biological evaluation of a series of macrocyclic hybrids and analogues of the antimitotic natural products dictyostatin, discodermolide, and taxol.

Authors:  Ian Paterson; Guy J Naylor; Nicola M Gardner; Esther Guzmán; Amy E Wright
Journal:  Chem Asian J       Date:  2010-10-28

9.  Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

Authors:  Zhihong Huang; Ei-ichi Negishi
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

10.  Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins.

Authors:  Brendan L Quigley; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-02       Impact factor: 9.825
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