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  • Title: Synthetic studies of tedanolide, a marine macrolide displaying potent antitumor activity. Stereoselective synthesis of the C13-C23 segment.
    Author: Iwata Y, Tanino K, Miyashita M.
    Journal: Org Lett; 2005 Jun 09; 7(12):2341-4. PubMed ID: 15932193.
    Abstract:
    [structure: see text] A highly stereoselective synthesis of the C13-C23 segment of tedanolide (1), an 18-membered macrolide isolated from the Caribbean sponge Tedania ignis, displaying significant cytotoxicity against KB and PS tumor cell lines, is described which involves two stereoselective epoxidations of regioisomeric trisubstituted double bonds and a stereospecific S(N)2' methylation reaction of a trans-gamma,delta-epoxy-cis-alpha,beta-unsaturated ester as the key steps.
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