Literature DB >> 20359229

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

Jennifer M Finefield1, Robert M Williams.   

Abstract

An efficient total synthesis of notoamide J, a new prenylated indole alkaloid and potential biosynthetic precursor, is described herein. Starting from L-proline and a substituted tryptophan derivative, this synthesis also employs an oxidation and pinacol rearrangement for the formation of the oxindole in the final step.

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Year:  2010        PMID： 20359229      PMCID： PMC2862136          DOI： 10.1021/jo100332c

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


  19 in total

1.  New paraherquamide antibiotics with anthelmintic activity.

Authors:  S E Blanchflower; R M Banks; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1991-05       Impact factor: 2.649

2.  A concise total synthesis of the notoamides C and D.

Authors:  Alan W Grubbs; Gerald D Artman; Sachiko Tsukamoto; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Notoamides A-D: prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp.

Authors:  Hikaru Kato; Takushi Yoshida; Takanori Tokue; Yuka Nojiri; Hiroshi Hirota; Tomihisa Ohta; Robert M Williams; Sachiko Tsukamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

5.  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

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

Authors:  R M Banks; S E Blanchflower; J R Everett; B R Manger; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1997-10       Impact factor: 2.649

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.

Authors:  J M Liesch; C F Wichmann
Journal:  J Antibiot (Tokyo)       Date:  1990-11       Impact factor: 2.649

9.  Sclerotiamide: a new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum.

Authors:  A C Whyte; J B Gloer; D T Wicklow; P F Dowdw
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

10.  Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A.

Authors:  Barry B Snider; Hongbo Zeng
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354
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  8 in total

1.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

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

Authors:  James D Sunderhaus; David H Sherman; Robert M Williams
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

3.  Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids.

Authors:  Shengying Li; Jennifer M Finefield; James D Sunderhaus; Timothy J McAfoos; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2011-12-28       Impact factor: 15.419

4.  Studies on the biosynthesis of the notoamides: synthesis of an isotopomer of 6-hydroxydeoxybrevianamide E and biosynthetic incorporation into notoamide J.

Authors:  Jennifer M Finefield; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  J Org Chem       Date:  2011-06-28       Impact factor: 4.354

5.  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

6.  Palladium-catalyzed synthesis of N-tert-prenylindoles.

Authors:  Kirsten F Johnson; Ryan Van Zeeland; Levi M Stanley
Journal:  Org Lett       Date:  2013-05-28       Impact factor: 6.005

Review 7.  Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.

Authors:  Kimberly R Klas; Hikaru Kato; Jens C Frisvad; Fengan Yu; Sean A Newmister; Amy E Fraley; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

Review 8.  Marine Indole Alkaloids.

Authors:  Natalie Netz; Till Opatz
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118
  8 in total

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