Literature DB >> 15646954

Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Timothy W Funk1, Jon Efskind, Robert H Grubbs.   

Abstract

[Reaction: see text] Various substituted conjugated dienes have been made by olefin cross-metathesis. Using either electronic or steric "protection," one of the olefins of the conjugated diene was deactivated relative to the other for cross-metathesis. The reactions proceed with very high chemoselectivity and, when steric deactivation is used, very high diastereoselectivity.

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Year:  2005        PMID： 15646954     DOI： 10.1021/ol047929z

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


  14 in total

1.  Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Authors:  Pilho Kim; Yong-Mei Zhang; Gautham Shenoy; Quynh-Anh Nguyen; Helena I Boshoff; Ujjini H Manjunatha; Michael B Goodwin; John Lonsdale; Allen C Price; Darcie J Miller; Ken Duncan; Stephen W White; Charles O Rock; Clifton E Barry; Cynthia S Dowd
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

2.  Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors:  Rodrigo B Andrade; Stephen F Martin
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

3.  Z-selective metathesis homocoupling of 1,3-dienes by molybdenum and tungsten monoaryloxide pyrrolide (MAP) complexes.

Authors:  Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-07-02       Impact factor: 15.419

4.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation.

Authors:  Jong-Rock Kong; Chang-Woo Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

5.  Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.

Authors:  Gustavo Moura-Letts; Dennis P Curran
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

6.  Concise syntheses of insect pheromones using Z-selective cross metathesis.

Authors:  Myles B Herbert; Vanessa M Marx; Richard L Pederson; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-10       Impact factor: 15.336

Review 7.  Recent advances in ruthenium-based olefin metathesis.

Authors:  O M Ogba; N C Warner; D J O'Leary; R H Grubbs
Journal:  Chem Soc Rev       Date:  2018-06-18       Impact factor: 54.564

8.  Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.

Authors:  Wei Zhu; María Jiménez; Won-Hyuk Jung; Daniel P Camarco; Raghavan Balachandran; Andreas Vogt; Billy W Day; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

9.  Efficient, divergent synthesis of cryptophycin unit A analogues.

Authors:  Kyle L Bolduc; Scott D Larsen; David H Sherman
Journal:  Chem Commun (Camb)       Date:  2012-05-22       Impact factor: 6.222

10.  Alkene chemoselectivity in ruthenium-catalyzed Z-selective olefin metathesis.

Authors:  Jeffrey S Cannon; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336
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