Literature DB >> 21245309

Diversity-oriented synthesis leads to an effective class of bifunctional linchpins uniting anion relay chemistry (ARC) with benzyne reactivity.

Amos B Smith1, Won-Suk Kim.   

Abstract

In conjunction with the construction of a diversity-oriented synthesis library of 10-membered ring "natural product-like" macrolides, the design, synthesis, and validation of a unique class of bifunctional linchpins, uniting benzyne reactivity initiated by type II anion relay chemistry (ARC) has been achieved, permitting access to diverse [2+2], [3+2], and [4+2] cycloadducts.

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Year:  2011        PMID： 21245309      PMCID： PMC3084103          DOI： 10.1073/pnas.1015265108

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  18 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Domino Reactions in Organic Synthesis.

Authors:  Lutz F. Tietze
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  Multicomponent Reactions with Isocyanides.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-15       Impact factor: 15.336

4.  Novel phenalenone derivatives from a marine-derived fungus exhibit distinct inhibition spectra against eukaryotic DNA polymerases.

Authors:  Marinela Perpelescu; Jun'ichi Kobayashi; Miho Furuta; Yasutomo Ito; Shunji Izuta; Masaharu Takemura; Motoshi Suzuki; Shonen Yoshida
Journal:  Biochemistry       Date:  2002-06-18       Impact factor: 3.162

5.  Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors:  Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

6.  Total synthesis of the neotropical poison-frog alkaloid (-)-205B.

Authors:  Amos B Smith; Dae-Shik Kim
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

7.  The [1,5]-Brook rearrangement: an initial application in anion relay chemistry.

Authors:  Amos B Smith; Ming Xian; Won-Suk Kim; Dae-Shik Kim
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

8.  Benzyl and phenylthiomethyl silanes: a new class of bifunctional linchpins for type II anion relay chemistry (ARC).

Authors:  Amos B Smith; Rongbiao Tong
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

9.  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

Review 10.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384
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  12 in total

Review 1.  Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.

Authors:  Yifan Deng; Amos B Smith
Journal:  Acc Chem Res       Date:  2020-04-09       Impact factor: 22.384

2.  Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C-H silylation of phenols with traceless acetal directing groups.

Authors:  Parham Asgari; Udaya Sree Dakarapu; Hiep H Nguyen; Junha Jeon
Journal:  Tetrahedron       Date:  2016-12-08       Impact factor: 2.457

3.  Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via type II anion relay chemistry.

Authors:  Amos B Smith; Heeoon Han; Won-Suk Kim
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

4.  Design, synthesis, and biological evaluation of diminutive forms of (+)-spongistatin 1: lessons learned.

Authors:  Amos B Smith; Christina A Risatti; Onur Atasoylu; Clay S Bennett; Junke Liu; Hongsheng Cheng; Karen TenDyke; Qunli Xu
Journal:  J Am Chem Soc       Date:  2011-08-12       Impact factor: 15.419

5.  A unified synthetic strategy to the Cryptocarya family of natural products exploiting Anion Relay Chemistry (ARC).

Authors:  Bruno Melillo; Amos B Smith
Journal:  Org Lett       Date:  2013-04-24       Impact factor: 6.005

6.  Long-range anion relay chemistry (LR-ARC): a validated ARC tactic.

Authors:  Luis Sanchez; Amos B Smith
Journal:  Org Lett       Date:  2012-12-06       Impact factor: 6.005

7.  Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Xuemei Wan; Jane E Ishmael; Kerry L McPhail; Amos B Smith
Journal:  J Org Chem       Date:  2018-02-26       Impact factor: 4.354

8.  Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.

Authors:  Heeoon Han; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

Review 9.  Natural Products as a Foundation for Drug Discovery.

Authors:  John A Beutler
Journal:  Curr Protoc Pharmacol       Date:  2019-09

10.  Total Synthesis of (-)-Secu'amamine A Exploiting Type II Anion Relay Chemistry.

Authors:  Heeoon Han; Amos B Smith
Journal:  Org Lett       Date:  2015-08-20       Impact factor: 6.005
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