Literature DB >> 16209529

A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans.

Barry M Trost1, Hanbiao Yang, Georg Wuitschik.   

Abstract

[reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran.

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Year:  2005        PMID： 16209529     DOI： 10.1021/ol0520065

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


  11 in total

1.  Synthesis of a ring-expanded bryostatin analogue.

Authors:  Barry M Trost; Hanbiao Yang; Oliver R Thiel; Alison J Frontier; Cheyenne S Brindle
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

2.  Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process.

Authors:  T Andrew Mitchell; Cunxiang Zhao; Daniel Romo
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

3.  Total synthesis of bryostatin 16 using a Pd-catalyzed diyne coupling as macrocyclization method and synthesis of C20-epi-bryostatin 7 as a potent anticancer agent.

Authors:  Barry M Trost; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2010-11-02       Impact factor: 15.419

4.  Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

Authors:  David S Barnett; Scott E Schaus
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

Review 5.  Transition metal-catalyzed couplings of alkynes to 1,3-enynes: modern methods and synthetic applications.

Authors:  Barry M Trost; James T Masters
Journal:  Chem Soc Rev       Date:  2016-02-01       Impact factor: 54.564

6.  Total syntheses of bryostatins: synthesis of two ring-expanded bryostatin analogues and the development of a new-generation strategy to access the C7-C27 fragment.

Authors:  Barry M Trost; Hanbiao Yang; Guangbin Dong
Journal:  Chemistry       Date:  2011-07-21       Impact factor: 5.236

7.  Atom-economic and stereoselective syntheses of the ring a and B subunits of the bryostatins.

Authors:  Barry M Trost; Hanbiao Yang; Cheyenne S Brindle; Guangbin Dong
Journal:  Chemistry       Date:  2011-07-19       Impact factor: 5.236

8.  Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

Authors:  Barry M Trost; Alicia C Gutierrez; Robert C Livingston
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

9.  Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Nature       Date:  2008-11-27       Impact factor: 49.962

Review 10.  Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.

Authors:  Haruhiko Fuwa
Journal:  Mar Drugs       Date:  2016-03-25       Impact factor: 5.118
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