Literature DB >> 17580906

Practical synthesis of 7-prenylindole.

Xin Xiong1, Michael C Pirrung.   

Abstract

7-Prenylindole is a useful building block for natural product and natural product analogue synthesis. While there have been several past syntheses of 7-prenylindole, none of them is very practical for its preparation on scale. Using an aza-Claisen rearrangement as the key step, 7-prenylindole has been prepared in four steps from indoline in 62% overall yield.

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Year:  2007        PMID： 17580906      PMCID： PMC2556248          DOI： 10.1021/jo070734v

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


  11 in total

1.  Short and convergent synthesis of asterriquinone B1 and demethylasterriquinone B1.

Authors:  K Tatsuta; H Mukai; K Mitsumoto
Journal:  J Antibiot (Tokyo)       Date:  2001-01       Impact factor: 2.649

2.  Total Synthesis of (-)-Muscoride A.

Authors:  Peter Wipf; Srikanth Venkatraman
Journal:  J Org Chem       Date:  1996-09-20       Impact factor: 4.354

3.  [Contents of tropical medicinal plants. 29. Synthesis of Annonidin B].

Authors:  H Achenbach; D Franke
Journal:  Arch Pharm (Weinheim)       Date:  1987-06       Impact factor: 3.751

4.  Antitumor activity of asterriquinones from Aspergillus fungi. IV. An attempt to modify the structure of asterriquinones to increase the activity.

Authors:  S Shimizu; Y Yamamoto; S Koshimura
Journal:  Chem Pharm Bull (Tokyo)       Date:  1982-05       Impact factor: 1.645

5.  Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1.

Authors:  Michael C Pirrung; Zhitao Li; Kaapjoo Park; Jin Zhu
Journal:  J Org Chem       Date:  2002-11-15       Impact factor: 4.354

6.  Composition of the leaf, stem bark and root bark oils of Isolona cooperi investigated by GC (retention index), GC-MS and 13C-NMR spectroscopy.

Authors:  Jean Brice Boti; Gérard Koukoua; Thomas Yao N'Guessan; Alain Muselli; Antoine-François Bernardini; Joseph Casanova
Journal:  Phytochem Anal       Date:  2005 Sep-Oct       Impact factor: 3.373

7.  Antiinflammatory agents. 3. Synthesis and pharmacological evaluation of 2-amino-3-benzoylphenylacetic acid and analogues.

Authors:  D A Walsh; H W Moran; D A Shamblee; I M Uwaydah; W J Welstead; L F Sancilio; W N Dannenburg
Journal:  J Med Chem       Date:  1984-11       Impact factor: 7.446

8.  Total Synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl aza-Claisen rearrangement.

Authors:  Jennifer M Roe; Richard A B Webster; A Ganesan
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

9.  Synthesis of 2,5-dihydroxy-3-(indol-3-yl)benzoquinones by acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone.

Authors:  Michael C Pirrung; Liu Deng; Zhitao Li; Kaapjoo Park
Journal:  J Org Chem       Date:  2002-11-29       Impact factor: 4.354

10.  Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids.

Authors:  Christian G Hartung; Anja Fecher; Brian Chapell; Victor Snieckus
Journal:  Org Lett       Date:  2003-05-29       Impact factor: 6.005
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  1 in total

1.  Direct prenylation of aromatic and alpha,beta-unsaturated carboxamides via iridium-catalyzed C-H oxidative addition-allene insertion.

Authors:  Yong Jian Zhang; Eduardas Skucas; Michael J Krische
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005
  1 in total

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