Literature DB >> 11869136

Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction.

Taotao Ling1, Erwan Poupon, Erik J Rueden, Emmanuel A Theodorakis.   

Abstract

[reaction: see text] A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.

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Year:  2002        PMID： 11869136     DOI： 10.1021/ol025501z

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


  13 in total

1.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

2.  Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency.

Authors:  Jayasree M Srinivasan; Priya A Mathew; Amie L Williams; John C Huffman; Jeffrey N Johnston
Journal:  Chem Commun (Camb)       Date:  2011-02-24       Impact factor: 6.222

3.  Synthesis of (-)-callicarpenal, a potent arthropod-repellent.

Authors:  Taotao Ling; Jing Xu; Ryan Smith; Abbas Ali; Charles L Cantrell; Emmanuel A Theodorakis
Journal:  Tetrahedron       Date:  2011-04-29       Impact factor: 2.457

4.  Synthesis of an advanced intermediate en route to the mitomycin natural products.

Authors:  Amie L Williams; Jayasree M Srinivasan; Jeffrey N Johnston
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

5.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

Review 6.  Synthetic strategies to terpene quinones/hydroquinones.

Authors:  Marina Gordaliza
Journal:  Mar Drugs       Date:  2012-02-14       Impact factor: 6.085

7.  Selective nickel- and manganese-catalyzed decarboxylative cross coupling of some α,β-unsaturated carboxylic acids with cyclic ethers.

Authors:  Jia-Xiang Zhang; Yan-Jing Wang; Wei Zhang; Nai-Xing Wang; Cui-Bing Bai; Ya-Lan Xing; Yi-He Li; Jia-Long Wen
Journal:  Sci Rep       Date:  2014-12-12       Impact factor: 4.379

8.  Gold(I)-Catalyzed Synthesis of Indenes and Cyclopentadienes: Access to (±)-Laurokamurene B and the Skeletons of the Cycloaurenones and Dysiherbols.

Authors:  Xiang Yin; Mauro Mato; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

9.  Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Beilstein J Org Chem       Date:  2013-06-12       Impact factor: 2.883

Review 10.  Marine Invertebrate Metabolites with Anticancer Activities: Solutions to the "Supply Problem".

Authors:  Nelson G M Gomes; Ramesh Dasari; Sunena Chandra; Robert Kiss; Alexander Kornienko
Journal:  Mar Drugs       Date:  2016-05-21       Impact factor: 5.118
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