Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 13, Pages 4949-4955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800545r
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Funding
- NCI NIH HHS [R01 CA059515-07, CA 059515, R29 CA059515, R01 CA059515] Funding Source: Medline
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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. ne 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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