Literature DB >> 12589698

Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Robert M Williams1, Rhona J Cox.   

Abstract

Studies from our laboratories on the paraherquamide, brevianamide, and asperparaline families of natural products are reviewed. It has been proposed that the unique core ring system that is common to this family of compounds arises by a biological intramolecular Diels-Alder cycloaddition reaction. Key biosynthetic studies are described, along with classical synthetic approaches as well as those inspired by Nature for the synthesis of these interesting molecules.

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Year:  2003        PMID: 12589698     DOI: 10.1021/ar020229e

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  55 in total

1.  Notoamide E: Biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600.

Authors:  Jennifer M Finefield; Thomas J Greshock; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2011-04-20       Impact factor: 2.415

2.  Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.

Authors:  Yousong Ding; Jeffrey R de Wet; James Cavalcoli; Shengying Li; Thomas J Greshock; Kenneth A Miller; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2010-09-15       Impact factor: 15.419

3.  Studies Towards Paraherquamides E & F and Related C-labeled Putative Biosynthetic Intermediates: Stereocontrolled Synthesis of the α-Alkyl-β-Methylproline Ring System.

Authors:  Konrad Sommer; Robert M Williams
Journal:  Tetrahedron       Date:  2008-07-21       Impact factor: 2.457

4.  Electrocatalytic multicomponent assembling of isatins, 3-methyl-2-pyrazolin-5-ones and malononitrile: facile and convenient way to functionalized spirocyclic [indole-3,4'-pyrano[2,3-c]pyrazole] system.

Authors:  Michail N Elinson; Alexander S Dorofeev; Fedor M Miloserdov; Gennady I Nikishin
Journal:  Mol Divers       Date:  2008-12-02       Impact factor: 2.943

Review 5.  Enantiomeric natural products: occurrence and biogenesis.

Authors:  Jennifer M Finefield; David H Sherman; Martin Kreitman; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-03       Impact factor: 15.336

6.  Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Authors:  Sunkyu Han; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-10-31       Impact factor: 4.354

7.  Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide.

Authors:  Jacob G Robins; Kyu J Kim; Alex J Chinn; John S Woo; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2016-02-26       Impact factor: 4.354

8.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B.

Authors:  James D Sunderhaus; Timothy J McAfoos; Jennifer M Finefield; Hikaru Kato; Shengying Li; Sachiko Tsukamoto; David H Sherman; Robert M Williams
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005

10.  Calmodulin inhibitory activity of the malbrancheamides and various analogs.

Authors:  Kenneth A Miller; Mario Figueroa; Meriah W N Valente; Thomas J Greshock; Rachel Mata; Robert M Williams
Journal:  Bioorg Med Chem Lett       Date:  2008-10-17       Impact factor: 2.823

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