Literature DB >> 18497934

The oxa-Michael reaction: from recent developments to applications in natural product synthesis.

Carl F Nising1, Stefan Bräse.   

Abstract

In marked contrast to Michael reactions, oxa-Michael reactions have not been used as standard transformations in organic synthesis until quite recently. This was mainly due to a lack of reactivity and selectivity, although the potential products of such reactions are valuable intermediates. This tutorial review presents recent major advances in the field of oxa-Michael (sometimes called oxo-Michael or oxy-Michael) reactions and applications in the total synthesis of complex natural products.

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Year:  2008        PMID: 18497934     DOI: 10.1039/b718357g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  38 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

2.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

3.  Total synthesis and absolute stereochemical assignment of kibdelone C.

Authors:  David L Sloman; Jeffrey W Bacon; John A Porco
Journal:  J Am Chem Soc       Date:  2011-06-15       Impact factor: 15.419

4.  Concise syntheses of the abyssinones and discovery of new inhibitors of prostate cancer and MMP-2 expression.

Authors:  Rebecca L Farmer; Margaret M Biddle; Antoinette E Nibbs; Xiaoke Huang; Raymond C Bergan; Karl A Scheidt
Journal:  ACS Med Chem Lett       Date:  2010-11-11       Impact factor: 4.345

5.  Cu(II)-catalyzed olefin migration and Prins cyclization: highly diastereoselective synthesis of substituted tetrahydropyrans.

Authors:  Arun K Ghosh; Daniel R Nicponski
Journal:  Org Lett       Date:  2011-07-28       Impact factor: 6.005

6.  Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization.

Authors:  Arun K Ghosh; Jorden Kass; Daniel R Nicponski; Chad Keyes
Journal:  Synthesis (Stuttg)       Date:  2012-12       Impact factor: 3.157

7.  Gold (III) Chloride-Catalyzed 6-endo-trig Oxa-Michael Addition Reactions for Diastereoselective Synthesis of Fused Tetrahydropyranones.

Authors:  Jennifer Ciesielski; David Lebœuf; Harry A Stern; Alison J Frontier
Journal:  Adv Synth Catal       Date:  2013-07-08       Impact factor: 5.837

8.  An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans.

Authors:  Ansoo Lee; Rick C Betori; Erika A Crane; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2018-05-10       Impact factor: 15.419

Review 9.  New synthetic triterpenoids: potent agents for prevention and treatment of tissue injury caused by inflammatory and oxidative stress.

Authors:  Michael B Sporn; Karen T Liby; Mark M Yore; Liangfeng Fu; Justin M Lopchuk; Gordon W Gribble
Journal:  J Nat Prod       Date:  2011-02-10       Impact factor: 4.050

10.  A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids.

Authors:  Vera Lúcia Patrocinio Pereira; André Luiz da Silva Moura; Daniel Pais Pires Vieira; Leandro Lara de Carvalho; Eliz Regina Bueno Torres; Jeronimo da Silva Costa
Journal:  Beilstein J Org Chem       Date:  2013-04-30       Impact factor: 2.883

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