Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 8, Pages 2479-2483Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9916535
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Funding
- NCI NIH HHS [CA 42056] Funding Source: Medline
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A concise, efficient approach to the total synthesis of ningalin B (1) based on a heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine -> 1,2-diazine -> pyrrole) ideally suited for construction of the densely functionalized pyrrole core found in the natural product is detailed. Examination of the natural product and a number of synthetic intermediates revealed that while lacking inherent cytotoxic activity, many reverse the multidrug-resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.
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