Literature DB >> 17973484

Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.

Zhushou Luo1, Katherine Peplowski, Gary A Sulikowski.   

Abstract

The BC ring system of upenamide was assembled using a stereoselective Diels-Alder reaction followed by a Staudinger/aza-Wittig/imine hydrolysis reaction. Stereoselective aldol coupling with an aldehyde that incorporates the DE ring system led to an advanced synthetic intermediate en route to the marine alkaloid upenamide.

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Year:  2007        PMID： 17973484      PMCID： PMC2534099          DOI： 10.1021/ol702255k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  'Upenamide: An unprecedented macrocyclic alkaloid from the Indonesian sponge Echinochalina sp.

Authors:  J I Jiménez; G Goetz; C M Mau; W Y Yoshida; P J Scheuer; R T Williamson; M Kelly
Journal:  J Org Chem       Date:  2000-12-15       Impact factor: 4.354

2.  A Short Total Synthesis of Kuehneromycin A This work was generously supported by the Deutsche Forschungsgemeinschaft and the Fazit-Stiftung. We are grateful to Prof. W. Steglich, Ludwig-Maximilians-Universität München, for copies of spectra of natural kuehneromycin A and for recording 600 MHz (1)H NMR spectra of our synthetic sample. We thank BASF AG, Ludwigshafen, Germany, Pfizer AG, Karlsruhe, Germany, Haarmann & Reimer GmbH, Holzminden, Germany, Wacker GmbH, Burghausen, Germany, DEGUSSA AG, Frankfurt a. M., Germany and Bayer AG, Leverkusen, Germany, for chemicals and laboratory equipment.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-04       Impact factor: 15.336

3.  Synthesis of (+/-)-phloeodictine A1.

Authors:  Bobbianna J Neubert; Barry B Snider
Journal:  Org Lett       Date:  2003-03-06       Impact factor: 6.005

4.  Biogenesis of 3-alkylpyridine alkaloids in the marine mollusc Haminoea orbignyana.

Authors:  Adele Cutignano; Annabella Tramice; Salvatore De Caro; Guido Villani; Guido Cimino; Angelo Fontana
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-16       Impact factor: 15.336

5.  Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide.

Authors:  Kurt Kiewel; Zhushou Luo; Gary A Sulikowski
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

6.  Enantioselective synthesis of marine indole alkaloid hamacanthin B.

Authors:  Biao Jiang; Cai-Guang Yang; Jun Wang
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

Review 7.  The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters.

Authors:  Elias J Corey; Angel Guzman-Perez
Journal:  Angew Chem Int Ed Engl       Date:  1998-03-02       Impact factor: 15.336

8.  The first synthesis of the ABC-ring system of 'upenamide.

Authors:  Jan Peter Schmidt; Sandra Beltrán-Rodil; Rhona J Cox; Graeme D McAllister; Mark Reid; Richard J K Taylor
Journal:  Org Lett       Date:  2007-09-01       Impact factor: 6.005
  8 in total
  1 in total

1.  A concise Diels-Alder strategy leading to congeners of the ABC ring system of the marine alkaloid 'upenamide.

Authors:  Marta E Wenzler; Bruce J Melancon; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2016-06-07       Impact factor: 2.415
  1 in total

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