Literature DB >> 22488814

Scalable total synthesis of (-)-berkelic acid by using a protecting-group-free strategy.

Francisco J Fañanás1, Abraham Mendoza, Tamara Arto, Baris Temelli, Félix Rodríguez.   

Abstract

Supply chain: the polycyclic core of (-)-berkelic acid (1) was constructed in just one step from very simple starting materials. The total synthesis of 1 involves a seven-step linear sequence. Protection/deprotection steps were avoided and all but the last step were performed on a gram scale. This synthesis could solve the supply problem associated with the exhaustion of the natural source.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22488814     DOI: 10.1002/anie.201109076

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


  4 in total

1.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  A biosynthetically inspired synthesis of (-)-berkelic acid and analogs.

Authors:  Christopher F Bender; Christopher L Paradise; Vincent M Lynch; Francis K Yoshimoto; Jef K De Brabander
Journal:  Tetrahedron       Date:  2018-01-12       Impact factor: 2.457

3.  Solvent-dependent divergent functions of Sc(OTf)₃ in stereoselective epoxide-opening spiroketalizations.

Authors:  Indrajeet Sharma; Jacqueline M Wurst; Derek S Tan
Journal:  Org Lett       Date:  2014-04-17       Impact factor: 6.005

Review 4.  Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules.

Authors:  Thilo Focken; Stephen Hanessian
Journal:  Beilstein J Org Chem       Date:  2014-08-13       Impact factor: 2.883

  4 in total

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