Literature DB >> 15901191

Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems.

Robert S Coleman1, Matthew C Walczak.   

Abstract

[structure: see text]. The synthesis of a hetero-bis-metallo 1,3-butadiene is reported, and its use as an orthogonal Stille and Suzuki-Miyaura coupling partner is detailed. The tin/boron diene participated successfully in a one-pot, sequential Stille and Suzuki-Miyaura coupling protocol, and its utility was demonstrated in the two-step construction of the pentaene side chain of the Fusarium metabolite lucilactaene.

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Year:  2005        PMID: 15901191     DOI: 10.1021/ol050768u

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


  7 in total

1.  Borostannylation of alkynes and enynes. Scope and limitations of the reaction and utility of the adducts.

Authors:  Ramakrishna Reddy Singidi; T V RajanBabu
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling.

Authors:  Suk Joong Lee; Kaitlyn C Gray; James S Paek; Martin D Burke
Journal:  J Am Chem Soc       Date:  2008-01-16       Impact factor: 15.419

3.  Iterative Cross-Couplng with MIDA Boronates: Towards a General Platform for Small Molecule Synthesis.

Authors:  Eric P Gillis; Martin D Burke
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

4.  Total synthesis of (+)-superstolide A.

Authors:  Mariola Tortosa; Neal A Yakelis; William R Roush
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

5.  (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.

Authors:  Amos B Smith; Megan A Foley; Shuzhi Dong; Alia Orbin
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

6.  1-(Triethoxysilyl)buta-1,3-dienes-New Building Blocks for Stereoselective Synthesis of Unsymmetrical (E,E)-1,4-Disubstituted 1,3-dienes.

Authors:  Justyna Szudkowska-Frątczak; Mariusz Taczała; Piotr Pawluć
Journal:  Materials (Basel)       Date:  2015-10-28       Impact factor: 3.623

7.  A Synthetic Small Molecule F240B Decreases NLRP3 Inflammasome Activation by Autophagy Induction.

Authors:  Chun-Hsien Wu; Chin Heng Gan; Lan-Hui Li; Jen-Che Chang; Shin-Tai Chen; Mridula P Menon; Shu-Meng Cheng; Shih-Ping Yang; Chen-Lung Ho; Oleg V Chernikov; Chi-Hung Lin; Yulin Lam; Kuo-Feng Hua
Journal:  Front Immunol       Date:  2020-12-18       Impact factor: 7.561

  7 in total

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