Literature DB >> 18816134

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

Panduka B Koswatta1, Rasapalli Sivappa, H V Rasika Dias, Carl J Lovely.   

Abstract

The first total synthesis of the Leucetta alkaloid calcaridine A is described based on a biosynthetic postulate. Application of an oxidative rearrangement of a 4,5-disubstituted imidazole leads to the formation of both calcaridine A and epi-calcaridine A. An X-ray crystal structure determination on the latter has allowed the assignment of the relative configuration of the epimeric natural product and calcaridine A by extrapolation.

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Year:  2008        PMID： 18816134      PMCID： PMC2650485          DOI： 10.1021/ol802018r

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


  14 in total

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2.  Studies toward the total synthesis of axinellamine and massadine.

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4.  Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange

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5.  A new structural theme in the imidazole-containing alkaloids from a calcareous Leucetta sponge.

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Journal:  J Org Chem       Date:  2004-12-24       Impact factor: 4.354

6.  Selective functionalization of imidazoles via an iodine-copper exchange reaction.

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Journal:  Chem Commun (Camb)       Date:  2006-04-20       Impact factor: 6.222

7.  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

8.  Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge.

Authors:  Ru Angelie Edrada; Chad C Stessman; Phillip Crews
Journal:  J Nat Prod       Date:  2003-07       Impact factor: 4.050

9.  Preparation and Diels-Alder chemistry of 4-vinylimidazoles.

Authors:  Carl J Lovely; Hongwang Du; Rasapalli Sivappa; Manojkumar R Bhandari; Yong He; H V Rasika Dias
Journal:  J Org Chem       Date:  2007-04-11       Impact factor: 4.354

10.  Oxidative rearrangement of imidazoles with dimethyldioxirane.

Authors:  Carl J Lovely; Hongwang Du; Yong He; H V Rasika Dias
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  8 in total

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Authors:  Heather M Lima; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2012-04-24       Impact factor: 6.005

3.  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

4.  Synthesis of 2-imidazolones and 2-iminoimidazoles.

Authors:  Heather M Lima; Carl J Lovely
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

5.  Total Syntheses of Naamidine G and 14-Methoxynaamidine G.

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Journal:  Tetrahedron Lett       Date:  2010-01-06       Impact factor: 2.415

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

Authors:  Panduka B Koswatta; Jayanta Das; Muhammed Yousufuddin; Carl J Lovely
Journal:  European J Org Chem       Date:  2015-04

7.  Total synthesis of the putative structure of nagelamide D.

Authors:  Manojkumar R Bhandari; Rasapalli Sivappa; Carl J Lovely
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

8.  Total syntheses of kealiinines A-C.

Authors:  Jayanta Das; Panduka B Koswatta; J Daniel Jones; Muhammed Yousufuddin; Carl J Lovely
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  8 in total

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