Literature DB >> 16836416

Total syntheses of (+/-)-cis-trikentrin A and (+/-)-cis-trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines.

Raymond J Huntley1, Raymond L Funk.   

Abstract

[Structure: see text] A convergent and versatile strategy for the diastereoselective syntheses of (+/-)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6pi-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.

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Year:  2006        PMID： 16836416     DOI： 10.1021/ol061259a

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


  13 in total

1.  Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

Authors:  Ryuji Hayashi; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development.

Authors:  Neil Brown; Diheng Luo; Joseph A Decapo; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-12-23       Impact factor: 2.415

3.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

4.  Regioselective Diels-Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes.

Authors:  Neil Brown; Diheng Luo; David Vandervelde; Shaorong Yang; Allen Brassfield; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-01-07       Impact factor: 2.415

5.  Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

Authors:  Wang Liu; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-13       Impact factor: 15.419

6.  Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.

Authors:  Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  ACS Comb Sci       Date:  2011-06-30       Impact factor: 3.784

7.  Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.

Authors:  Nalin Chandrasoma; Neil Brown; Allen Brassfield; Alok Nerurkar; Susana Suarez; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2013-02-20       Impact factor: 2.415

8.  Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditions.

Authors:  Ashley N Garr; Diheng Luo; Neil Brown; Christopher J Cramer; Keith R Buszek; David VanderVelde
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

9.  Concise total synthesis of (+/-)-cis-trikentrin A and (+/-)-herbindole A via intermolecular indole aryne cycloaddition.

Authors:  Keith R Buszek; Neil Brown; Diheng Luo
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

10.  Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Authors:  Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005
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