Literature DB >> 14518979

Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of avrainvillamide.

Andrew G Myers1, Seth B Herzon.   

Abstract

The 3-alkylidene-3H-indole 1-oxide functional group found in the naturally occurring alkaloid avrainvillamide has been synthesized by a cross coupling-reductive condensation sequence and found to undergo reversible addition of oxygen- and sulfur-based nucleophiles.

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Year:  2003        PMID： 14518979     DOI： 10.1021/ja0372006

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

1.  Evolution of a strategy for total synthesis of the marine fungal alkaloid (+/-)-communesin F.

Authors:  Jae Hong Seo; Peng Liu; Steven M Weinreb
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

2.  Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture.

Authors:  Jeremy E Wulff; Seth B Herzon; Romain Siegrist; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2007-03-31       Impact factor: 15.419

Review 3.  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

Review 4.  Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Authors:  Abraham J Waldman; Tai L Ng; Peng Wang; Emily P Balskus
Journal:  Chem Rev       Date:  2017-04-04       Impact factor: 60.622

Review 5.  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

6.  New synthetic technology for the construction of N-hydroxyindoles and synthesis of nocathiacin I model systems.

Authors:  K C Nicolaou; Anthony A Estrada; Graeme C Freestone; Sang Hyup Lee; Xavier Alvarez-Mico
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457

7.  The natural product avrainvillamide binds to the oncoprotein nucleophosmin.

Authors:  Jeremy E Wulff; Romain Siegrist; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2007-10-25       Impact factor: 15.419

8.  Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B.

Authors:  Gerald D Artman; Alan W Grubbs; Robert M Williams
Journal:  J Am Chem Soc       Date:  2007-04-25       Impact factor: 15.419

9.  An improved synthesis of alpha,beta-unsaturated nitrones relevant to the stephacidins and analogs thereof.

Authors:  Benjamin D Hafensteiner; María Escribano; Elena Petricci; Phil S Baran
Journal:  Bioorg Med Chem Lett       Date:  2009-04-18       Impact factor: 2.823

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

Authors:  Thomas J Greshock; Alan W Grubbs; Robert M Williams
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457
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