Literature DB >> 28933833

Total Synthesis of (-)-Nahuoic Acid Ci (Bii).

Qi Liu1, Yifan Deng1, Amos B Smith1.   

Abstract

A convergent total synthesis of (-)-nahuoic acid Ci(Bii) (3), a novel cis-decalin polyketide, has been achieved. Key synthetic transformations include Type II Anion Relay Chemistry (ARC) to construct the polyol chain, a Ti-catalyzed asymmetric Diels-Alder reaction to generate the cis-decalin skeleton, and a late-stage large fragment union exploiting a Micalizio alkoxide-directed alkyne-alkene coupling tactic.

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Year:  2017        PMID： 28933833      PMCID： PMC5655813          DOI： 10.1021/jacs.7b08683

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  26 in total

1.  A site- and stereoselective intermolecular alkene-alkyne coupling process.

Authors:  Holly A Reichard; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Total synthesis of kinamycins C, F, and J.

Authors:  K C Nicolaou; Hongming Li; Andrea L Nold; Doron Pappo; Achim Lenzen
Journal:  J Am Chem Soc       Date:  2007-08-04       Impact factor: 15.419

3.  Reaction design, discovery, and development as a foundation to function-oriented synthesis.

Authors:  Glenn C Micalizio; Sarah B Hale
Journal:  Acc Chem Res       Date:  2015-02-10       Impact factor: 22.384

4.  Asymmetric total synthesis of pinnaic acid.

Authors:  Shu Xu; Hirokazu Arimoto; Daisuke Uemura
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Synthesis of the DFGH ring system of type B physalins: highly oxygenated, cage-shaped molecules.

Authors:  Megumi Ohkubo; Go Hirai; Mikiko Sodeoka
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Modular synthesis of the C9-C27 degradation product of aflastatin A via alkyne-epoxide cross-couplings.

Authors:  Omar Robles; Frank E McDonald
Journal:  Org Lett       Date:  2008-04-10       Impact factor: 6.005

7.  Nahuoic acid A produced by a Streptomyces sp. isolated from a marine sediment is a selective SAM-competitive inhibitor of the histone methyltransferase SETD8.

Authors:  David E Williams; Doralyn S Dalisay; Fengling Li; James Amphlett; Wisanu Maneerat; Miguel Angel Garcia Chavez; Yan Alexander Wang; Teatulohi Matainaho; Wenyu Yu; Peter J Brown; Cheryl H Arrowsmith; Masoud Vedadi; Raymond J Andersen
Journal:  Org Lett       Date:  2012-12-28       Impact factor: 6.005

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.  Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.

Authors:  Qi Liu; Chihui An; Karen TenDyke; Hongsheng Cheng; Young Yongchun Shen; Adam T Hoye; Amos B Smith
Journal:  J Org Chem       Date:  2016-02-16       Impact factor: 4.354

10.  An Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16-C29 Fragment of Rhizopodin.

Authors:  Bruno Melillo; Ming Z Chen; Roberto Forestieri; Amos B Smith
Journal:  Org Lett       Date:  2015-12-07       Impact factor: 6.005
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  7 in total

1.  Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Authors:  Yifan Deng; Minh D Nguyen; Yike Zou; K N Houk; Amos B Smith
Journal:  Org Lett       Date:  2019-02-26       Impact factor: 6.005

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.  Merging Asymmetric [1,2]-Additions of Lithium Acetylides to Carbonyls with Type II Anion Relay Chemistry.

Authors:  Kevin T O'Brien; Amos B Smith
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

4.  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

Review 5.  Biologically active marine natural products and their molecular targets discovered using a chemical genetics approach.

Authors:  David E Williams; Raymond J Andersen
Journal:  Nat Prod Rep       Date:  2019-11-21       Impact factor: 13.423

Review 6.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

7.  Total synthesis of nahuoic acid A via a putative biogenetic intramolecular Diels-Alder (IMDA) reaction.

Authors:  Lucía Guillade; Paula Mora; Pedro Villar; Rosana Alvarez; Angel R de Lera
Journal:  Chem Sci       Date:  2021-10-27       Impact factor: 9.825
  7 in total

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