Literature DB >> 26257576

Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Panduka B Koswatta1, Jayanta Das1, Muhammed Yousufuddin2, Carl J Lovely1.   

Abstract

An exploration of an abiotic approach to spirocalcaridines A and B is described centered on electrophile-induced dearomatizing spirocyclization of aryl enyne derivatives. Elaboration of the α-iodoenone via an Ullmann-like, copper-catalyzed amidation provided a formamide which upon treatment with methylamine undergoes a dienol-arene rearrangement, providing the corresponding kealiinine-like framework. This observation suggests a possible biosynthetic links between the spirocalcaridines and the naphthimidazole group of Leucetta alkaloids.

Entities:  

Keywords:  2-Aminoimidazole; Dearomatization; Rearrangement; Spirocyclization; Ullman reaction

Year:  2015        PMID： 26257576      PMCID： PMC4524666          DOI： 10.1002/ejoc.201403650

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  23 in total

1.  Stereoselective synthesis of pyridinones: application to the synthesis of (-)-barrenazines.

Authors:  Thilo Focken; André B Charette
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

2.  Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs.

Authors:  Jayanta Das; Arunoday Bhan; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem Lett       Date:  2013-09-06       Impact factor: 2.823

3.  Oxidative reactions of tetrahydrobenzimidazole derivatives with N-sulfonyloxaziridines.

Authors:  Rasapalli Sivappa; Panduka Koswatta; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2007-08-13       Impact factor: 2.415

4.  Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.

Authors:  Panduka B Koswatta; Rasapalli Sivappa; H V Rasika Dias; Carl J Lovely
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

5.  Structure revision of spiroleucettadine, a sponge alkaloid with a bicyclic core meager in H-atoms.

Authors:  Kimberly N White; Taro Amagata; Allen G Oliver; Karen Tenney; Philip J Wenzel; Phillip Crews
Journal:  J Org Chem       Date:  2008-10-17       Impact factor: 4.354

6.  Selective synthesis of spiro[4,5]trienyl acetates via an intramolecular electrophilic ipso-iodocyclization process.

Authors:  Bo-Xiao Tang; Dong-Jun Tang; Shi Tang; Quan-Fu Yu; Yue-Hua Zhang; Yun Liang; Ping Zhong; Jin-Heng Li
Journal:  Org Lett       Date:  2008-02-15       Impact factor: 6.005

7.  Synthesis of the reported structures for kealiinines B and C.

Authors:  Joseph B Gibbons; Keith M Gligorich; Bryan E Welm; Ryan E Looper
Journal:  Org Lett       Date:  2012-09-11       Impact factor: 6.005

8.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

9.  New imidazole alkaloids from the Indonesian sponge Leucetta chagosensis.

Authors:  Wafaa Hassan; RuAngelie Edrada; Rainer Ebel; Victor Wray; Albrecht Berg; Rob van Soest; Sumali Wiryowidagdo; Peter Proksch
Journal:  J Nat Prod       Date:  2004-05       Impact factor: 4.050

10.  Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors:  Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005
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  1 in total

1.  Total synthesis and cytotoxicity of Leucetta alkaloids.

Authors:  Panduka B Koswatta; Sabha Kasiri; Jayanta K Das; Arunoday Bhan; Heather M Lima; Beatriz Garcia-Barboza; Nicole N Khatibi; Muhammed Yousufuddin; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem       Date:  2017-01-20       Impact factor: 3.641
  1 in total

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