Literature DB >> 15787519

Synthesis of the C(1)-C(25) fragment of amphidinol 3: application of the double-allylboration reaction for synthesis of 1,5-diols.

Eric M Flamme1, William R Roush.   

Abstract

[structure: see text] A synthesis of the C(1)-C(25) fragment of amphidinol 3 is described. The synthesis features two applications of double allylboration reaction methodology for the highly stereoselective synthesis of 1,5-diol units in the C(1)-C(15) segment.

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Year:  2005        PMID： 15787519     DOI： 10.1021/ol050250q

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


  14 in total

1.  Stereoselective synthesis of the C(1)-C(19) fragment of tetrafibricin.

Authors:  Ricardo Lira; William R Roush
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

2.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

3.  Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: application to the synthesis of the C(23)-C(40) fragment of tetrafibricin.

Authors:  Jeremy Kister; Philippe Nuhant; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Org Lett       Date:  2011-03-04       Impact factor: 6.005

4.  Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin.

Authors:  Philippe Nuhant; Jeremy Kister; Ricardo Lira; Achim Sorg; William R Roush
Journal:  Tetrahedron       Date:  2011-09-02       Impact factor: 2.457

5.  Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides.

Authors:  Joshua E Ney; Michael B Hay; Qifei Yang; John P Wolfe
Journal:  Adv Synth Catal       Date:  2005-10-01       Impact factor: 5.837

6.  Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Authors:  Ming Chen; Masaki Handa; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

7.  Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.

Authors:  Philippe Nuhant; William R Roush
Journal:  J Am Chem Soc       Date:  2013-03-26       Impact factor: 15.419

8.  Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anti-ene-diols as allylic triethylsilyl ethers.

Authors:  Jacqueline D Hicks; Chan Woo Huh; Ashley D Legg; William R Roush
Journal:  Org Lett       Date:  2007-11-21       Impact factor: 6.005

9.  Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction.

Authors:  John R Huckins; Javier de Vicente; Scott D Rychnovsky
Journal:  Org Lett       Date:  2007-10-18       Impact factor: 6.005

10.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419
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