Literature DB >> 26029849

Total Synthesis of (-)-Nodulisporic Acid D.

Yike Zou1, Jason E Melvin1, Stephen S Gonzales1, Matthew J Spafford1, Amos B Smith1.   

Abstract

A convergent total synthesis of the architecturally complex indole diterpenoid (-)-nodulisporic acid D has been achieved. Key synthetic transformations include vicinal difunctionalization of an advanced α,β-unsaturated aldehyde to form the E,F-trans-fused 5,6-ring system of the eastern hemisphere and a cascade cross-coupling/indolization protocol leading to the CDE multisubstituted indole core.

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Year:  2015        PMID： 26029849      PMCID： PMC4479160          DOI： 10.1021/jacs.5b04728

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


  28 in total

1.  Drug-resistant Drosophila indicate glutamate-gated chloride channels are targets for the antiparasitics nodulisporic acid and ivermectin.

Authors:  N S Kane; B Hirschberg; S Qian; D Hunt; B Thomas; R Brochu; S W Ludmerer; Y Zheng; M Smith; J P Arena; C J Cohen; D Schmatz; J Warmke; D F Cully
Journal:  Proc Natl Acad Sci U S A       Date:  2000-12-05       Impact factor: 11.205

2.  Nodulisporic acids C, C1, and C2: a series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.

Authors:  John G Ondeyka; Kevin Byrne; Diane Vesey; Deborah L Zink; Wesley L Shoop; Michael A Goetz; Sheo B Singh
Journal:  J Nat Prod       Date:  2003-01       Impact factor: 4.050

3.  An extremely active catalyst for the Negishi cross-coupling reaction.

Authors:  Jacqueline E Milne; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

4.  Nodulisporic acid A synthetic studies. 1. Overall strategy and construction of a western hemisphere subtarget.

Authors:  A B Smith; H Ishiyama; Y S Cho; K Ohmoto
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

5.  Nodulisporic acid A synthetic studies. 2. Construction of an eastern hemisphere subtarget.

Authors:  A B Smith; Y S Cho; H Ishiyama
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

6.  Indole diterpenoid synthetic studies. The total synthesis of (+)-nodulisporic acid F.

Authors:  Amos B Smith; Akin H Davulcu; Laszló Kürti
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

7.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

Review 8.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination.

Authors:  Mark Lautens; Yuan-Qing Fang
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

10.  Biosynthesis of nodulisporic acid A: precursor studies.

Authors:  Kevin M Byrne; Scott K Smith; John G Ondeyka
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419
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  11 in total

1.  Chemistry: Why synthesize?

Authors:  Philip Ball
Journal:  Nature       Date:  2015-12-17       Impact factor: 49.962

2.  Type II Anion Relay Chemistry: Conformational Constraints To Achieve Effective [1,5]-Vinyl Brook Rearrangements.

Authors:  Qi Liu; Yu Chen; Xiao Zhang; K N Houk; Yong Liang; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-06-14       Impact factor: 15.419

3.  Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

4.  Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.

Authors:  Nicole A Godfrey; Devon J Schatz; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2018-09-28       Impact factor: 15.419

5.  Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

Authors:  Kevin P C Minbiole
Journal:  J Antibiot (Tokyo)       Date:  2016-03-02       Impact factor: 2.649

6.  Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

7.  Discovery of Unclustered Fungal Indole Diterpene Biosynthetic Pathways through Combinatorial Pathway Reassembly in Engineered Yeast.

Authors:  Man-Cheng Tang; Hsiao-Ching Lin; Dehai Li; Yi Zou; Jian Li; Wei Xu; Ralph A Cacho; Maureen E Hillenmeyer; Neil K Garg; Yi Tang
Journal:  J Am Chem Soc       Date:  2015-10-21       Impact factor: 15.419

Review 8.  Total synthesis of architecturally complex indole terpenoids: strategic and tactical evolution.

Authors:  Yike Zou; Amos B Smith
Journal:  J Antibiot (Tokyo)       Date:  2017-08-30       Impact factor: 2.649

9.  A Concise Approach to Paxilline Indole Diterpenes.

Authors:  David T George; Eric J Kuenstner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2015-12-07       Impact factor: 15.419

Review 10.  Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies.

Authors:  Michael A Corsello; Junyong Kim; Neil K Garg
Journal:  Chem Sci       Date:  2017-06-27       Impact factor: 9.825
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