Literature DB >> 10217710

Oxidized welwitindolinones from terrestrial fischerella spp

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Abstract

3-Hydroxy-N-methylwelwitindolinone C isonitrile (3), 3-hydroxy-N-methylwelwitindolinone C isothiocyanate (4), and the novel cyclic ether N-methylwelwitindolinone D isonitrile (6) are three new alkaloids from two terrestrial Fischerella spp. belonging to the Stigonemataceae. Photooxidation of N-methylwelwitindolinone C isonitrile (1) leads to isonitriles 3 and 6. Isonitrile 3 is readily hydrated to 3-hydroxy-N-methylwelwitindolinone C formamide (5), an artifact produced during the isolation procedure.

Entities:  

Year:  1999        PMID： 10217710     DOI： 10.1021/np980485t

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  34 in total

1.  Total synthesis: Welwitindolinone is well worth it.

Authors:  John L Wood
Journal:  Nat Chem       Date:  2012-04-23       Impact factor: 24.427

2.  Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.

Authors:  Qunsheng Guo; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

3.  Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

Authors:  Jeremy M Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

4.  Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Authors:  Shunyan Mo; Aleksej Krunic; George Chlipala; Jimmy Orjala
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050

5.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

6.  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

Review 7.  Chemodiversity in freshwater and terrestrial cyanobacteria - a source for drug discovery.

Authors:  George E Chlipala; Shunyan Mo; Jimmy Orjala
Journal:  Curr Drug Targets       Date:  2011-10       Impact factor: 3.465

8.  Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.

Authors:  Matthew L Hillwig; Heather A Fuhrman; Kuljira Ittiamornkul; Tyler J Sevco; Daniel H Kwak; Xinyu Liu
Journal:  Chembiochem       Date:  2014-03-21       Impact factor: 3.164

9.  Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.

Authors:  Rebecca E Johnson; Hwisoo Ree; Marco Hartmann; Laura Lang; Shota Sawano; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

10.  Access to a welwitindolinone core using sequential cycloadditions.

Authors:  Barry M Trost; Patrick J McDougall
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005
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