Literature DB >> 20806914

Enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers using a cross-metathesis allylboration sequence.

SusAnn M Winbush1, William R Roush.   

Abstract

The enantioselective synthesis of (Z)-1,2-anti-2,5-anti-triol monosilyl ethers via a two-step sequence involving olefin cross-metathesis of β-alkoxyallylboronate 4 and subsequent allylboration of the derived bisboryl intermediate 6 provides triol monoethers 7 with good to excellent diastereoselectivity.

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Year:  2010        PMID： 20806914      PMCID： PMC2945398          DOI： 10.1021/ol101789g

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


  22 in total

1.  Simple, stable, and versatile double-allylation reagents for the stereoselective preparation of skeletally diverse compounds.

Authors:  Feng Peng; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2007-02-22       Impact factor: 15.419

2.  Effect of the allylic substituents on ring closing metathesis: the total synthesis of stagonolide B and 4-epi-stagonolide B.

Authors:  Awadut G Giri; Mohabul A Mondal; Vedavati G Puranik; Chepuri V Ramana
Journal:  Org Biomol Chem       Date:  2009-10-29       Impact factor: 3.876

3.  cis-gigantrionenin and 4-acetyl gigantetrocin A, two new bioactive annonaceous acetogenins from Goniothalamus giganteus, and the stereochemistries of acetogenin 1,2,5-triols.

Authors:  L Zeng; Y Zhang; Q Ye; G Shi; K He; J L McLaughlin
Journal:  Bioorg Med Chem       Date:  1996-08       Impact factor: 3.641

4.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

5.  Synthesis of the C(43)-C(67) fragment of amphidinol 3.

Authors:  Jacqueline D Hicks; Eric M Flamme; William R Roush
Journal:  Org Lett       Date:  2005-11-24       Impact factor: 6.005

6.  Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane.

Authors:  Jeremy Kister; Amy C DeBaillie; Ricardo Lira; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

7.  Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions.

Authors:  Soon Hyeok Hong; Michael W Day; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

8.  Total synthesis of platensimycin and related natural products.

Authors:  K C Nicolaou; Ang Li; David J Edmonds; G Scott Tria; Shelby P Ellery
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

9.  Synthesis of amphidinolide E C10-C26 fragment.

Authors:  Jorge Esteban; Anna M Costa; Jaume Vilarrasa
Journal:  Org Lett       Date:  2008-10-07       Impact factor: 6.005

10.  Borabicyclo[3.3.2]decanes and the stereoselective asymmetric synthesis of 1,3-diol stereotriads from 1,3-diborylpropenes.

Authors:  Ana Z González; José G Román; Eyleen Alicea; Eda Canales; John A Soderquist
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419
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  3 in total

1.  Total synthesis of (-)-tirandamycin C.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-12-07       Impact factor: 6.005

2.  Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

Authors:  Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

3.  Synthesis of Z-(pinacolato)allylboron and Z-(pinacolato)alkenylboron compounds through stereoselective catalytic cross-metathesis.

Authors:  Elizabeth T Kiesewetter; Robert V O'Brien; Elsie C Yu; Simon J Meek; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2013-04-15       Impact factor: 15.419
  3 in total

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