Literature DB >> 11082024

Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: approaches to diazonamide A.

D E Fuerst1, B M Stoltz, J L Wood.   

Abstract

[reaction: see text] Two complementary strategies for the synthesis of the diazonamide A bisaryl quaternary center are described. The first strategy relies upon an extremely facile tandem cyclopropanation/ring-opening sequence, which has proven amenable to chiral catalysis to provide enantioenriched material. The second strategy relies upon a more concise alkylation route ideal for material advancement.

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Year:  2000        PMID： 11082024     DOI： 10.1021/ol006578v

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


  5 in total

Review 1.  Diazo Compounds: Versatile Tools for Chemical Biology.

Authors:  Kalie A Mix; Matthew R Aronoff; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2016-10-26       Impact factor: 5.100

2.  Azonazine, a novel dipeptide from a Hawaiian marine sediment-derived fungus, Aspergillus insulicola.

Authors:  Quan-Xiang Wu; Mitchell S Crews; Marija Draskovic; Johann Sohn; Tyler A Johnson; Karen Tenney; Frederick A Valeriote; Xiao-Jun Yao; Leonard F Bjeldanes; Phillip Crews
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  An expedient formal total synthesis of (-)-diazonamide A via a powerful, stereoselective O-aryl to C-aryl migration to form the C10 quaternary center.

Authors:  Chi-Ming Cheung; Frederick W Goldberg; Philip Magnus; Claire J Russell; Rachel Turnbull; Vince Lynch
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

4.  Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.

Authors:  Alexander A Fadeev; Alexey O Chagarovskiy; Anton S Makarov; Irina I Levina; Olga A Ivanova; Maxim G Uchuskin; Igor V Trushkov
Journal:  Molecules       Date:  2020-12-05       Impact factor: 4.411

5.  Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.

Authors:  Ivan A Andreev; Nina K Ratmanova; André U Augustin; Olga A Ivanova; Irina I Levina; Victor N Khrustalev; Daniel B Werz; Igor V Trushkov
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336
  5 in total

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