Literature DB >> 17249768

Asymmetric total synthesis of nigerone.

Evan S Divirgilio1, Elizabeth C Dugan, Carol A Mulrooney, Marisa C Kozlowski.   

Abstract

[reaction: see text] An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone is reported. The key step was an eight-step isomerization process to form the final natural product. The isomerization precursor was constructed via asymmetric oxidative biaryl coupling of an advanced intermediate with a 1,5-diaza-cis-decalin copper catalyst.

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Year:  2007        PMID： 17249768     DOI： 10.1021/ol062468y

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


  9 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

Review 3.  Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling.

Authors:  Marisa C Kozlowski; Barbara J Morgan; Elizabeth C Linton
Journal:  Chem Soc Rev       Date:  2009-09-23       Impact factor: 54.564

4.  Enantioselective total synthesis of (S)-bisoranjidiol, an axially chiral bisanthraquinone.

Authors:  Erin E Podlesny; Marisa C Kozlowski
Journal:  Org Lett       Date:  2012-02-24       Impact factor: 6.005

5.  Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether.

Authors:  Erin E Podlesny; Marisa C Kozlowski
Journal:  J Nat Prod       Date:  2012-06-12       Impact factor: 4.050

6.  Mild aromatic palladium-catalyzed protodecarboxylation: kinetic assessment of the decarboxylative palladation and the protodepalladation steps.

Authors:  Joshua S Dickstein; John M Curto; Osvaldo Gutierrez; Carol A Mulrooney; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

7.  Perylenequinone natural products: enantioselective synthesis of the oxidized pentacyclic core.

Authors:  Carol A Mulrooney; Barbara J Morgan; Xiaolin Li; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

8.  Mechanistic study of asymmetric oxidative biaryl coupling: evidence for self-processing of the copper catalyst to achieve control of oxidase vs oxygenase activity.

Authors:  J Brian Hewgley; Shannon S Stahl; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-08-19       Impact factor: 15.419

9.  Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones.

Authors:  Lorenzo Di Terlizzi; Simone Scaringi; Carlotta Raviola; Riccardo Pedrazzani; Marco Bandini; Maurizio Fagnoni; Stefano Protti
Journal:  J Org Chem       Date:  2022-03-22       Impact factor: 4.354
  9 in total

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