Literature DB >> 21668016

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.

Paul D Thornton1, Neil Brown, David Hill, Ben Neuenswander, Gerald H Lushington, Conrad Santini, Keith R Buszek.   

Abstract

The construction of an unprecedented class of an indole-based library, namely, a 6,7-annulated-4-substituted 93-member indole library, using a strategic combination of 6,7-indolyne cycloaddition and cross-coupling reactions under both Suzuki-Miyaura and Buchwald-Hartwig conditions is described. This work represents the first example of library development that employs the indole aryne methodology. Annulated indoles, with the exception of only a few biologically active natural products (i.e., the trikentrins, herbindoles, teleocidins, and nodulisporic acids), have no representation in the PubChem or MLSMR databases. These structural entities are therefore predicted to have unique chemical property space characteristics and a high probability of exhibiting interesting biological activity.

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Year:  2011        PMID： 21668016      PMCID： PMC3959986          DOI： 10.1021/co2000289

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN： 2156-8944            Impact factor:   3.784


  23 in total

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

Authors:  Stephen K Jackson; Michael A Kerr
Journal:  J Org Chem       Date:  2007-01-26       Impact factor: 4.354

2.  Isolation and structure elucidation of teleocidin B-1, B-2, B-3, and B-4.

Authors:  Y Hitotsuyanagi; H Fujiki; M Suganuma; N Aimi; S Sakai; Y Endo; K Shudo; T Sugimura
Journal:  Chem Pharm Bull (Tokyo)       Date:  1984-10       Impact factor: 1.645

3.  Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors:  G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

4.  An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: discovery of macrocyclic histone deacetylase inhibitors.

Authors:  Lisa A Marcaurelle; Eamon Comer; Sivaraman Dandapani; Jeremy R Duvall; Baudouin Gerard; Sarathy Kesavan; Maurice D Lee; Haibo Liu; Jason T Lowe; Jean-Charles Marie; Carol A Mulrooney; Bhaumik A Pandya; Ann Rowley; Troy D Ryba; Byung-Chul Suh; Jingqiang Wei; Damian W Young; Lakshmi B Akella; Nathan T Ross; Yan-Ling Zhang; Daniel M Fass; Surya A Reis; Wen-Ning Zhao; Stephen J Haggarty; Michelle Palmer; Michael A Foley
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

5.  Indolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applications.

Authors:  Sarah M Bronner; Kevin B Bahnck; Neil K Garg
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

6.  Indolyne and aryne distortions and nucleophilic regioselectivites.

Authors:  Paul H-Y Cheong; Robert S Paton; Sarah M Bronner; G-Yoon J Im; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

7.  Design and synthesis of medium-ring lactam libraries inspired by octalactin a. A convergent-divergent approach.

Authors:  Neil Brown; Ge Gao; Machiko Minatoya; Baohan Xie; David Vandervelde; Gerald H Lushington; Jean-Pierre H Perchellet; Elisabeth M Perchellet; Kyle R Crow; Keith R Buszek
Journal:  J Comb Chem       Date:  2008-08-12

8.  Synthesis of a natural product-inspired eight-membered ring lactam library via ring-closing metathesis.

Authors:  Neil Brown; Baohan Xie; Nataliya Markina; David Vandervelde; Jean-Pierre H Perchellet; Elisabeth M Perchellet; Kyle R Crow; Keith R Buszek
Journal:  Bioorg Med Chem Lett       Date:  2008-07-24       Impact factor: 2.823

9.  Improved method for the diimide reduction of multiple bonds on solid-supported substrates.

Authors:  Keith R Buszek; Neil Brown
Journal:  J Org Chem       Date:  2007-03-17       Impact factor: 4.354

10.  Indole diterpene synthetic studies: development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B.

Authors:  Amos B Smith; László Kürti; Akin H Davulcu; Young Shin Cho; Kazuyuki Ohmoto
Journal:  J Org Chem       Date:  2007-05-19       Impact factor: 4.354
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  10 in total

1.  An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors:  Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

2.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

3.  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

4.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

5.  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

6.  Regioselectivity of Diels-Alder Reactions Between 6,7-Dehydrobenzofuran and 2-Substituted Furans.

Authors:  Neil Brown; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2012-08-01       Impact factor: 2.415

7.  NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.

Authors:  Jian-Qiang Huang; Meng Yu; Xuefeng Yong; Chun-Yu Ho
Journal:  Nat Commun       Date:  2022-07-16       Impact factor: 17.694

8.  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

9.  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

10.  Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2.

Authors:  Noah F Fine Nathel; Tejas K Shah; Sarah M Bronner; Neil K Garg
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825
  10 in total

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