These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Total synthesis of the polyene-polyol macrolide RK-397, featuring cross-couplings of alkynylepoxide modules.
    Author: Burova SA, McDonald FE.
    Journal: J Am Chem Soc; 2004 Mar 03; 126(8):2495-500. PubMed ID: 14982459.
    Abstract:
    The total synthesis of the natural product RK-397 is based on a new synthetic strategy for assembling polyacetate structures, by efficient cross-coupling of nucleophilic terminal alkyne modules with electrophilic epoxides bearing another alkyne at the opposite terminus. The natural product is constructed from four principal modules: a polyene precursor for carbons 3-9, and three alkyne-terminated modules for carbons 10-16, 17-22, and 23-33. Each module is prepared with control of all stereochemical elements, and the alkynyl alcohols obtained from alkyne-epoxide couplings are converted into 1,3-diols by a sequence of hydroxyl-directed hydrosilylation, C-Si bond oxidation, and stereoselective ketone reduction with induction from the beta-hydroxyl group. The highly convergent nature of our synthetic pathway and the flexibility of the modular synthesis strategy for virtually any stereoisomer can provide access to other members of the polyene-polyol macrolides, including stereoisomers of RK-397.
    [Abstract] [Full Text] [Related] [New Search]