Literature DB >> 22415889

Total syntheses of the elusive welwitindolinones with bicyclo[4.3.1] cores.

Alexander D Huters1, Evan D Styduhar, Neil K Garg.   

Abstract

The welwitindolinones with bicyclo[4.3.1] cores are a class of natural products that have attracted tremendous interest from the synthetic community because of their fascinating structures and promising biological profiles. More than 15 research groups worldwide have reported progress toward these elusive natural products. This Minireview describes contemporary studies aimed at the total synthesis of these challenging targets, in addition to the two recently completed syntheses of welwitindolinones with bicyclo[4.3.1] cores reported by Rawal and Garg in 2011. Both of the completed efforts rely on C4-C11 bond constructions to access the congested bicyclic framework of these elusive natural products.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22415889     DOI: 10.1002/anie.201107567

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


  12 in total

1.  Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

2.  Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.

Authors:  Simon Hardy; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-10-07       Impact factor: 2.457

3.  Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines.

Authors:  Sergiy V Chepyshev; J Armando Lujan-Montelongo; Allen Chao; Fraser F Fleming
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-13       Impact factor: 15.336

4.  Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition.

Authors:  Min Zhang; Weiping Tang
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

5.  Formal syntheses of naturally occurring welwitindolinones.

Authors:  Tsung-hao Fu; William T McElroy; Mariam Shamszad; Stephen F Martin
Journal:  Org Lett       Date:  2012-07-25       Impact factor: 6.005

6.  Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

Authors:  Tsung-Hao Fu; William T McElroy; Mariam Shamszad; Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

7.  Annulation reactions of allenyl esters: an approach to bicyclic diones and medium-sized rings.

Authors:  Bilal A Bhat; Samantha L Maki; Elijah J St Germain; Pradip Maity; Salvatore D Lepore
Journal:  J Org Chem       Date:  2014-09-16       Impact factor: 4.354

8.  Total synthesis of (-)-N-methylwelwitindolinone B isothiocyanate via a chlorinative oxabicycle ring-opening strategy.

Authors:  Nicholas A Weires; Evan D Styduhar; Emma L Baker; Neil K Garg
Journal:  J Am Chem Soc       Date:  2014-10-10       Impact factor: 15.419

Review 9.  Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.

Authors:  Robert M Hohlman; David H Sherman
Journal:  Nat Prod Rep       Date:  2021-09-23       Impact factor: 15.111

10.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

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