Literature DB >> 16268528

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

Kurt Kiewel1, Zhushou Luo, Gary A Sulikowski.   

Abstract

[reaction: see text] A stereocontrolled synthesis of the DE fragment (2) of the marine alkaloid upenamide (1) is described. The synthesis proceeds in 12 steps from caprolactone (10) and 20-25% overall yield.

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Year:  2005        PMID： 16268528     DOI： 10.1021/ol051993e

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


  5 in total

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

Authors:  Zhushou Luo; Katherine Peplowski; Gary A Sulikowski
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005

2.  Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines.

Authors:  Hanmo Zhang; E Ben Hay; Steven J Geib; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

3.  Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Authors:  Hanmo Zhang; Kyu Ok Jeon; E Ben Hay; Steven J Geib; Dennis P Curran; Matthew G LaPorte
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

4.  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

5.  Pentannulation of N-heterocycles by a tandem gold-catalyzed [3,3]-rearrangement/Nazarov reaction of propargyl ester derivatives: a computational study on the crucial role of the nitrogen atom.

Authors:  Giovanna Zanella; Martina Petrović; Dina Scarpi; Ernesto G Occhiato; Enrique Gómez-Bengoa
Journal:  Beilstein J Org Chem       Date:  2020-12-15       Impact factor: 2.883
  5 in total

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