Jump to main content
Jump to site search

Issue 3, 2012
Previous Article Next Article

Nickel-catalyzed regiodivergent approach to macrolide motifs

Author affiliations

Abstract

A strategy for regiochemical reversal of reductive macrocyclizations of aldehydes and terminal alkynes has been developed. Using an advanced synthetic intermediate directed towards the methymycin/neomethymycin class of macrolides, selective endocyclization provides the natural twelve-membered ring series, whereas ligand alteration enables selective exocyclization to provide access to the unnatural eleven-membered ring series. The twelve-membered ring adduct was converted to 10-deoxymethynolide, completing an efficient total synthesis of this natural product.

Graphical abstract: Nickel-catalyzed regiodivergent approach to macrolide motifs

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Oct 2011, accepted on 02 Dec 2011 and first published on 06 Dec 2011


Article type: Edge Article
DOI: 10.1039/C2SC00866A
Citation: Chem. Sci., 2012,3, 892-895
  •   Request permissions

    Nickel-catalyzed regiodivergent approach to macrolide motifs

    A. Shareef, D. H. Sherman and J. Montgomery, Chem. Sci., 2012, 3, 892
    DOI: 10.1039/C2SC00866A

Search articles by author

Spotlight

Advertisements