Synthesis and evaluation of the cytotoxicity of apoptolidinones A and D |
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Authors: | Ghidu Victor P Wang Jingqi Wu Bin Liu Qingsong Jacobs Aaron Marnett Lawrence J Sulikowski Gary A |
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Institution: | Department of Chemistry, Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA. |
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Abstract: | 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). |
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