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: Stereoselective total synthesis of (-)-spirofungin A by utilising hydrogen-bond controlled spiroketalisation.
    Author: Lynch JE, Zanatta SD, White JM, Rizzacasa MA.
    Journal: Chemistry; 2011 Jan 03; 17(1):297-304. PubMed ID: 21207625.
    Abstract:
    The stereoselective total synthesis of the spiroketal containing Streptomyces metabolite (-)-spirofungin A (1) is described. A key step involved a spiroketalisation controlled by an intramolecular H-bond which favoured the desired spiroketal 4 (13:1 ratio). The presence of the intramolecular H-bond in 4 is possibly due to a 1,5-alkyne-oxygen interaction. Other key steps include an efficient cross-metathesis to form the spiroketal precursor, a tin mediated syn-aldol reaction and a Stille cross-coupling reaction to create the C22C23 bond. A final Wittig extension followed by deprotection gave (-)-spirofungin A (1).
    [Abstract] [Full Text] [Related] [New Search]