Literature DB >> 15939330

Synthetic approaches towards structurally diverse gamma-butyrolactone natural-product-like compounds.

Michael Seitz1, Oliver Reiser.   

Abstract

Natural products containing a gamma-butyrolactone ring are abundant in nature; however, few general synthetic approaches to their stereoselective synthesis with broad structural variety are known. In this article, recent developments towards mono- and polycyclic gamma-butyrolactone natural products and analogs are discussed. A special focus is given to asymmetric methods applying transition metal or organocatalysts that allow not only the efficient introduction of a broad variety of functional groups but ideally also the flexible construction of various natural-product-like, polycyclic scaffolds from common precursors.

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Year:  2005        PMID: 15939330     DOI: 10.1016/j.cbpa.2005.03.005

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  21 in total

1.  The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

Authors:  Arthur J Catino; Jason M Nichols; Brian J Nettles; Michael P Doyle
Journal:  J Am Chem Soc       Date:  2006-05-03       Impact factor: 15.419

2.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

3.  Phosphine-catalyzed asymmetric additions of malonate esters to {gamma}-substituted allenoates and allenamides.

Authors:  Riccardo Sinisi; Jianwei Sun; Gregory C Fu
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-12       Impact factor: 11.205

4.  Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-28       Impact factor: 15.336

5.  Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal.

Authors:  Carina I Jette; Z Jaron Tong; Ryan G Hadt; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-16       Impact factor: 15.336

6.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

7.  Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

Authors:  Stephen N Greszler; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls.

Authors:  Tao Liang; Wandi Zhang; Te-Yu Chen; Khoa D Nguyen; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-09-29       Impact factor: 15.419

9.  Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration.

Authors:  Heather E Burks; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

10.  Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts.

Authors:  Nicholas J Peraino; Sven H Kaster; Kraig A Wheeler; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-12-09       Impact factor: 4.354

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