Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D.

Ghidu VP, Wang J, Wu B, Liu Q, Jacobs A, Marnett LJ, Sulikowski GA
J Org Chem. 2008 73 (13): 4949-55

PMID: 18543990 · PMCID: PMC2572754 · DOI:10.1021/jo800545r

Apoptolidins A-D are microbial secondary metabolites shown to be selectively cytotoxic against several cancer cell lines and noncytotoxic against normal cells. Total syntheses of apoptolidinones A and D are reported. The efficient synthetic strategy leading to the apoptolidinones features construction of the common 20-membered macrolactone by an intramolecular Suzuki reaction and stereocontrolled aldol reactions establishing the C19/C20 and C22/C23 stereocenters. In contrast to apoptolidin A, the aglycones apoptolidinone A and D were shown to be noncytotoxic when evaluated against human lung cancer cells (H292).

MeSH Terms (6)

Antineoplastic Agents Cell Line, Tumor Humans Macrolides Molecular Structure Pyrones

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