Literature DB >> 28809569

Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Christian A Malapit1, Irungu K Luvaga1, Donald R Caldwell1, Nicholas K Schipper1, Amy R Howell1.   

Abstract

A one-step preparation of 3,4-disubstituted β-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to α-methylene-β-lactones is described. The operationally simple, stereoselective transformation provides a broad range of β-lactones from individual α-methylene-β-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone, an antimicrobial natural product.

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Year:  2017        PMID： 28809569      PMCID： PMC5834916          DOI： 10.1021/acs.orglett.7b01994

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


  49 in total

1.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds.

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Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  A strategy for dual inhibition of the proteasome and fatty acid synthase with belactosin C-orlistat hybrids.

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Journal:  Bioorg Med Chem       Date:  2017-01-19       Impact factor: 3.641

3.  Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

Authors:  Gang Chen; Norihito Tokunaga; Tamio Hayashi
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

4.  Practical, catalytic, asymmetric synthesis of beta-lactones via a sequential ketene dimerization/hydrogenation process: inhibitors of the thioesterase domain of fatty acid synthase.

Authors:  Vikram C Purohit; Robyn D Richardson; Jeffrey W Smith; Daniel Romo
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

5.  β-Lactone natural products and derivatives inactivate homoserine transacetylase, a target for antimicrobial agents.

Authors:  Gianfranco De Pascale; Ishac Nazi; Paul H M Harrison; Gerard D Wright
Journal:  J Antibiot (Tokyo)       Date:  2011-04-27       Impact factor: 2.649

6.  Synthesis of novel beta-lactone inhibitors of fatty acid synthase.

Authors:  Robyn D Richardson; Gil Ma; Yatsandra Oyola; Manuel Zancanella; Lynn M Knowles; Piotr Cieplak; Daniel Romo; Jeffrey W Smith
Journal:  J Med Chem       Date:  2008-08-19       Impact factor: 7.446

7.  Stereoselective synthesis of pyroglutamate natural product analogs from α- aminoacids and their anti-cancer evaluation.

Authors:  Srinivas Tekkam; Mohammad A Alam; Matthew J Just; Steven M Berry; Joseph L Johnson; Subash C Jonnalagadda; Venkatram R Mereddy
Journal:  Anticancer Agents Med Chem       Date:  2013-12       Impact factor: 2.505

8.  Rhodium-catalyzed Heck-type reaction of arylboronic acids with alpha,beta-unsaturated esters: tuning beta-hydrogen elimination vs. hydrolysis of alkylrhodium species.

Authors:  Gang Zou; Zhiyong Wang; Junru Zhu; Jie Tang
Journal:  Chem Commun (Camb)       Date:  2003-10-07       Impact factor: 6.222

9.  Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents.

Authors:  Kun Wei; Gang-Qiang Wang; Xue Bai; Yan-Fen Niu; He-Ping Chen; Chun-Nan Wen; Zheng-Hui Li; Ze-Jun Dong; Zhi-Li Zuo; Wen-Yong Xiong; Ji-Kai Liu
Journal:  Nat Prod Bioprospect       Date:  2015-06-18

10.  Remodeling natural products: chemistry and serine hydrolase activity of a rocaglate-derived β-lactone.

Authors:  Neil J Lajkiewicz; Armand B Cognetta; Micah J Niphakis; Benjamin F Cravatt; John A Porco
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419
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  2 in total

Review 1.  Indolylboronic Acids: Preparation and Applications.

Authors:  Marek Čubiňák; Tereza Edlová; Peter Polák; Tomáš Tobrman
Journal:  Molecules       Date:  2019-09-28       Impact factor: 4.411

2.  Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones.

Authors:  Yao Ge; Fei Ye; Jiawang Liu; Ji Yang; Anke Spannenberg; Haijun Jiao; Ralf Jackstell; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-17       Impact factor: 15.336
  2 in total

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