Literature DB >> 32077289

Concise Formal Synthesis of the Pseudopterosins via Anionic Oxy-Cope/Transannular Michael Addition Cascade.

Vincenzo Ramella1, Philipp C Roosen1, Christopher D Vanderwal1,2.   

Abstract

An anionic oxy-Cope/transannular Michael addition cascade converts a spirocyclic architecture-readily available by Diels-Alder cycloaddition-into the hydrophenalene carbon skeleton of the pseudopterosin aglycones. Oxidation of the resulting cyclohexenone ring to the phenol that is characteristic of the targets completes a short formal synthesis.

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Year:  2020        PMID： 32077289      PMCID： PMC7278522          DOI： 10.1021/acs.orglett.0c00486

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

1.  A Formal Enantiospecific Synthesis of 7,20-Diisocyanoadociane.

Authors:  Philipp C Roosen; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-10       Impact factor: 15.336

Review 2.  Total synthesis of the pseudopterosin aglycones.

Authors:  Christopher G Newton; Michael S Sherburn
Journal:  Nat Prod Rep       Date:  2015-06       Impact factor: 13.423

3.  Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems.

Authors:  Paul D Thornton; T Stanley Cameron; D Jean Burnell
Journal:  Org Biomol Chem       Date:  2011-03-22       Impact factor: 3.876

4.  Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20-Diisocyanoadociane.

Authors:  Alexander S Karns; Bryan D Ellis; Philipp C Roosen; Zeinab Chahine; Karine G Le Roch; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336

Review 5.  Marine diterpene glycosides.

Authors:  Fabrice Berrué; Malcolm W B McCulloch; Russell G Kerr
Journal:  Bioorg Med Chem       Date:  2011-07-02       Impact factor: 3.641

6.  Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions.

Authors:  Christopher G Newton; Samuel L Drew; Andrew L Lawrence; Anthony C Willis; Michael N Paddon-Row; Michael S Sherburn
Journal:  Nat Chem       Date:  2014-11-17       Impact factor: 24.427

7.  Enantioselective Total Syntheses of Various Amphilectane and Serrulatane Diterpenoids via Cope Rearrangements.

Authors:  Xuerong Yu; Fan Su; Chang Liu; Haosen Yuan; Shan Zhao; Zhiyao Zhou; Tianfei Quan; Tuoping Luo
Journal:  J Am Chem Soc       Date:  2016-05-10       Impact factor: 15.419

8.  Synthesis and potent antimalarial activity of kalihinol B.

Authors:  Mary Elisabeth Daub; Jacques Prudhomme; Karine Le Roch; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

9.  The Marine Natural Product Pseudopterosin Blocks Cytokine Release of Triple-Negative Breast Cancer and Monocytic Leukemia Cells by Inhibiting NF-κB Signaling.

Authors:  Julia Sperlich; Russell Kerr; Nicole Teusch
Journal:  Mar Drugs       Date:  2017-08-23       Impact factor: 5.118

10.  Pseudopterosin Inhibits Proliferation and 3D Invasion in Triple-Negative Breast Cancer by Agonizing Glucocorticoid Receptor Alpha.

Authors:  Julia Sperlich; Nicole Teusch
Journal:  Molecules       Date:  2018-08-10       Impact factor: 4.411
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  3 in total

1.  Evolution of a Short and Stereocontrolled Synthesis of (+)-7,20-Diisocyanoadociane.

Authors:  Philipp C Roosen; Alexander S Karns; Bryan D Ellis; Christopher D Vanderwal
Journal:  J Org Chem       Date:  2022-01-06       Impact factor: 4.198

2.  Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions.

Authors:  Natalie C Dwulet; Vincenzo Ramella; Christopher D Vanderwal
Journal:  Org Lett       Date:  2021-12-06       Impact factor: 6.005

Review 3.  A look around the West Indies: The spices of life are secondary metabolites.

Authors:  Adrian Demeritte; William M Wuest
Journal:  Bioorg Med Chem       Date:  2020-10-01       Impact factor: 3.641
  3 in total

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