Literature DB >> 20180531

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

Amos B Smith1, Rongbiao Tong.   

Abstract

A new class of bifunctional linchpins bearing electrophilic sites beta or gamma to a silyl group have been designed, synthesized, and demonstrated to be competent in tricomponent unions exploiting Type II Anion Relay Chemistry (ARC). High diastereoselectivities were observed when a phenyl moiety (R(2)) served as an anion-stabilizing group (ASG) adjacent to a methyl susbtituent (R(1)), while diastereomeric mixtures were obtained when a phenylthiol moiety served as the ASG, irrespective of alpha-substitution.

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Year:  2010        PMID： 20180531      PMCID： PMC2844645          DOI： 10.1021/ol100130x

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


  14 in total

1.  The Spongistatins: Architecturally Complex Natural Products-Part Two: Synthesis of the C(29-51) Subunit, Fragment Assembly, and Final Elaboration to (+)-Spongistatin 2 Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, a NIH Postdoctoral Fellowship to C.S.B., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr George T. Furst, Dr. Patrick J. Carroll, and Dr. Rakesh Kohli of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra, respectively.

Authors:  Amos B. Smith III; Qiyan Lin; Victoria A. Doughty; Linghang Zhuang; Mark D. McBriar; Jeffrey K. Kerns; Christopher S. Brook; Noriaki Murase; Kiyoshi Nakayama
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

2.  The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment Financial support was provided by the National Institutes of Health (National Cancer Institute) through Grant CA-70329, NIH Postdoctoral Fellowships to A.M.B. and W.H.M., a Japan Society for Promotion of Science Fellowship to N.M., and a Royal Society Fulbright Fellowship to V.A.D. We also thank the Daiichi Pharmaceutical Co., Ltd, and the Tanabe Seiyaku Co., Ltd for financial support. Finally we thank Dr. George T. Furst, Dr. Patrick J. Carroll, Dr. Rakesh Kohli, and Mr John Dykins of the University of Pennsylvania Spectroscopic Service Center for assistance in securing and interpreting high-field NMR spectra, X-ray crystal structures, and mass spectra.

Authors:  Amos B. Smith III; Victoria A. Doughty; Qiyan Lin; Linghang Zhuang; Mark D. McBriar; Armen M. Boldi; William H. Moser; Noriaki Murase; Kiyoshi Nakayama; Masao Sobukawa
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

3.  Anion relay chemistry: an effective tactic for diversity oriented synthesis.

Authors:  Amos B Smith; Ming Xian
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

4.  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

5.  Anion relay chemistry extended. Synthesis of a gorgonian sesquiterpene.

Authors:  Amos B Smith; Dae-Shik Kim; Ming Xian
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

6.  The spirastrellolides: construction of the southern C(1)-C(25) fragment exploiting anion relay chemistry.

Authors:  Amos B Smith; Dae-Shik Kim
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

7.  Enantio- and diastereoselective tandem zn-promoted brook rearrangement/ene-allene carbocyclization reaction.

Authors:  Rozalia Unger; Fritz Weisser; Nicka Chinkov; Amnon Stanger; Theodore Cohen; Ilan Marek
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

8.  (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.

Authors:  Amos B Smith; Megan A Foley; Shuzhi Dong; Alia Orbin
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

9.  Evolution of dithiane-based strategies for the construction of architecturally complex natural products.

Authors:  Amos B Smith; Christopher M Adams
Journal:  Acc Chem Res       Date:  2004-06       Impact factor: 22.384

10.  Diastereoselective Brook rearrangement-mediated [3+4] annulation: application to a formal synthesis of (+)-laurallene.

Authors:  Michiko Sasaki; Azusa Hashimoto; Koudai Tanaka; Masatoshi Kawahata; Kentaro Yamaguchi; Kei Takeda
Journal:  Org Lett       Date:  2008-04-08       Impact factor: 6.005
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  11 in total

1.  Anion relay chemistry: access to the type II ARC reaction manifold through a fundamentally different reaction pathway exploiting 1-oxa-2-silacyclopentanes and related congeners.

Authors:  Amos B Smith; Rongbiao Tong; Won-Suk Kim; William A Maio
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-10       Impact factor: 15.336

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

Authors:  Amos B Smith; Won-Suk Kim
Journal:  Proc Natl Acad Sci U S A       Date:  2011-01-18       Impact factor: 11.205

Review 3.  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

4.  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

5.  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

6.  Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.

Authors:  Joseph J Topczewski; John G Kodet; David F Wiemer
Journal:  J Org Chem       Date:  2011-01-12       Impact factor: 4.354

7.  Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Authors:  Stephanie A Murray; Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

8.  Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

Authors:  Baris Yucel; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-11-24       Impact factor: 5.837

9.  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

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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