Literature DB >> 18345688

Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

Kenneth A Miller1, Timothy R Welch, Thomas J Greshock, Yousong Ding, David H Sherman, Robert M Williams.   

Abstract

The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.

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Year:  2008        PMID： 18345688      PMCID： PMC2837585          DOI： 10.1021/jo800116y

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  16 in total

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2.  A concise, biomimetic total synthesis of stephacidin A and notoamide B.

Authors:  Thomas J Greshock; Alan W Grubbs; Sachiko Tsukamoto; Robert M Williams
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4.  Reversal of P-glycoprotein mediated multidrug resistance in K562 cell line by a novel synthetic calmodulin inhibitor, E6.

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Journal:  Biol Pharm Bull       Date:  2005-10       Impact factor: 2.233

5.  Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides.

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Review 6.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

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Review 7.  Total synthesis and biosynthesis of the paraherquamides: an intriguing story of the biological Diels-Alder construction.

Authors:  Robert Michael Williams
Journal:  Chem Pharm Bull (Tokyo)       Date:  2002-06       Impact factor: 1.645

8.  Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G.

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9.  Improved biomimetic total synthesis of D,L-stephacidin A.

Authors:  Thomas J Greshock; Robert M Williams
Journal:  Org Lett       Date:  2007-09-14       Impact factor: 6.005

10.  Concise, Biomimetic Total Synthesis of d,l-Marcfortine C.

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  15 in total

1.  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

2.  Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

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Review 3.  Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors:  Kenneth A Miller; Robert M Williams
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

Review 4.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

5.  Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.

Authors:  Jennifer M Finefield; Robert M Williams
Journal:  J Org Chem       Date:  2010-05-07       Impact factor: 4.354

Review 6.  Fungal origins of the bicyclo[2.2.2]diazaoctane ring system of prenylated indole alkaloids.

Authors:  Jennifer M Finefield; Jens C Frisvad; David H Sherman; Robert M Williams
Journal:  J Nat Prod       Date:  2012-04-15       Impact factor: 4.050

7.  Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus.

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Journal:  J Org Chem       Date:  2011-06-29       Impact factor: 4.354

8.  Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.

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9.  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

10.  Comparative analysis of the biosynthetic systems for fungal bicyclo[2.2.2]diazaoctane indole alkaloids: the (+)/(-)-notoamide, paraherquamide and malbrancheamide pathways.

Authors:  Shengying Li; Krithika Anand; Hong Tran; Fengan Yu; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Sachiko Tsukamoto; Robert M Williams; David H Sherman
Journal:  Medchemcomm       Date:  2012-08       Impact factor: 3.597
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