Literature DB >> 17256909

Total synthesis of (+/-)-herbindole A, (+/-)-herbindole B, and (+/-)-cis-trikentrin A.

Stephen K Jackson1, Michael A Kerr.   

Abstract

Herein we describe a divergent total synthesis of the title compounds utilizing Diels-Alder reactions of monoimine quinoids, followed by cyclization of the aromatized adducts to generate the tricyclic skeletons. Elaboration to iodinated or triflated indole derivatives allows for installation of the requisite alkyl substitution via cross-coupling reactions.

Entities:  

Year:  2007        PMID： 17256909     DOI： 10.1021/jo062350v

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


  12 in total

1.  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

2.  A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions.

Authors:  Nalin Chandrasoma; Sivadarshini Pathmanathan; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  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

4.  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

5.  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

6.  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

7.  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

8.  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

9.  Antitumor effects of synthetic 6,7-annulated-4-substituted indole compounds in L1210 leukemic cells in vitro.

Authors:  Jean-Pierre H Perchellet; Andrew M Waters; Elisabeth M Perchellet; Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Nalin Chandrasoma; Keith R Buszek
Journal:  Anticancer Res       Date:  2012-11       Impact factor: 2.480

10.  Mechanisms by which synthetic 6,7-annulated-4-substituted indole compounds with anti-proliferative activity disrupt mitosis and block cytokinesis in human HL-60 tumor cells in vitro.

Authors:  Jean-Pierre H Perchellet; Elisabeth M Perchellet; Chingakham Ranjit Singh; Meghan T Monnett; Elizabeth R Studer; Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  Anticancer Res       Date:  2014-04       Impact factor: 2.480
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