Literature DB >> 19423345

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

Benjamin D Hafensteiner1, María Escribano, Elena Petricci, Phil S Baran.   

Abstract

A new method is reported for the synthesis of the alpha,beta-unsaturated nitrone moiety characteristic of the stephacidin/avrainvillamide family of bioactive prenylated indole alkaloids. Application to the synthesis of stephacidin analogs and a potential biological probe are showcased.

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Year:  2009        PMID： 19423345      PMCID： PMC2709696          DOI： 10.1016/j.bmcl.2009.04.045

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  17 in total

1.  Studies on the Biosynthesis of Paraherquamide: Synthesis and Incorporation of a Hexacyclic Indole Derivative as an Advanced Metabolite This work was supported by the National Institutes of Health (Grant no. CA70375 to R.M.W.). We wish to acknowledge the American Chemical Society Division of Organic Chemistry Fellowship (sponsored by SmithKline Beecham) and the Pharmacia-Upjohn Company for financial support (to E.M.S.). Mass spectra were obtained on instruments supported by the National Institutes of Health Shared Instrumentation Grant (No. GM49631). We also wish to thank Professor Dean Crick of the Department of Microbiology at Colorado State University for helpful discussions. J.F.S.-C. thanks the DGICYT of Spain for a research grant (project no. PB98-1438).

Authors:  Emily M. Stocking; Juan F. Sanz-Cervera; Robert M. Williams
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-01       Impact factor: 15.336

2.  Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells.

Authors:  Jingfang Qian-Cutrone; Stella Huang; Yue-Zhong Shu; Dolatrai Vyas; Craig Fairchild; Ana Menendez; Kimberly Krampitz; Richard Dalterio; Steven E Klohr; Qi Gao
Journal:  J Am Chem Soc       Date:  2002-12-11       Impact factor: 15.419

3.  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.

Authors:  Andrew G Myers; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2003-10-08       Impact factor: 15.419

Review 4.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

5.  Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B.

Authors:  Phil S Baran; Carlos A Guerrero; Benjamin D Hafensteiner; Narendra B Ambhaikar
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-20       Impact factor: 15.336

6.  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

7.  Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1h)-pyrazinones.

Authors:  S Jin; P Wessig; J Liebscher
Journal:  J Org Chem       Date:  2001-06-01       Impact factor: 4.354

Review 8.  Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report.

Authors:  Robert M Williams; Rhona J Cox
Journal:  Acc Chem Res       Date:  2003-02       Impact factor: 22.384

9.  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

10.  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
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  1 in total

1.  OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.

Authors:  Sean A Newmister; Claire M Gober; Stelamar Romminger; Fengan Yu; Ashootosh Tripathi; Lizbeth Lorena L Parra; Robert M Williams; Roberto G S Berlinck; Madeleine M Joullié; David H Sherman
Journal:  J Am Chem Soc       Date:  2016-08-24       Impact factor: 15.419
  1 in total

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