Literature DB >> 23614670

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

Bruno Melillo1, Amos B Smith.   

Abstract

A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.

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Year:  2013        PMID： 23614670      PMCID： PMC3671372          DOI： 10.1021/ol400857k

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


  21 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.  Iodo-cyclizations: novel strategy for the total syntheses of polyrhacitide A and epi-cryptocaryolone.

Authors:  Debendra K Mohapatra; Eswar Bhimireddy; P Sivarama Krishnarao; Pragna P Das; J S Yadav
Journal:  Org Lett       Date:  2011-01-07       Impact factor: 6.005

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.  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

5.  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

6.  An enantioselective synthesis of cryptocarya diacetate.

Authors:  T J Hunter; G A O'Doherty
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

7.  Synthesis and structure assignment of the minor metabolite arising from the frog pathogen Mycobacterium liflandii.

Authors:  Thomas Spangenberg; Sylvain Aubry; Yoshito Kishi
Journal:  Tetrahedron Lett       Date:  2010-03-31       Impact factor: 2.415

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.  Efficient asymmetric total syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate.

Authors:  Xiaolei Wang; Wenkuan Wang; Huaiji Zheng; Yingpeng Su; Tuo Jiang; Yongping He; Xuegong She
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

10.  A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones.

Authors:  Hua Wang; Brian J Shuhler; Ming Xian
Journal:  J Org Chem       Date:  2007-04-21       Impact factor: 4.354
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  12 in total

1.  Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane.

Authors:  Nisalak Trongsiriwat; Youge Pu; Yexenia Nieves-Quinones; Russell A Shelp; Marisa C Kozlowski; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

Review 2.  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

3.  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

4.  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

5.  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

6.  Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship.

Authors:  Yanping Wang; George A O'Doherty
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419

7.  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

8.  Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins.

Authors:  Ming Z Chen; Osvaldo Gutierrez; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-16       Impact factor: 15.336

9.  Type II Anion Relay Chemistry: Exploiting Bifunctional Weinreb Amide Linchpins for the One-Pot Synthesis of Differentiated 1,3-Diketones, Pyrans, and Spiroketals.

Authors:  Mark Farrell; Bruno Melillo; Amos B Smith
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-20       Impact factor: 15.336

10.  Total Synthesis of (-)-Mandelalide A Exploiting Anion Relay Chemistry (ARC): Identification of a Type II ARC/CuCN Cross-Coupling Protocol.

Authors:  Minh H Nguyen; Masashi Imanishi; Taichi Kurogi; Amos B Smith
Journal:  J Am Chem Soc       Date:  2016-03-08       Impact factor: 15.419
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