期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 7, 期 5, 页码 1052-1060出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201101021
关键词
cancer; cycloaddition; leukemia; natural products; total synthesis
资金
- National Institutes of Health (NIH) [R01 GM081484]
- National Science Foundation [CHE9709183, CHE0741968]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0741968] Funding Source: National Science Foundation
An efficient formal synthesis of (-)-englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell-lines. Our enantioselective strategy involved the construction of the BC ring system of compound 1 through a RhII-catalyzed [4+3] cycloaddition reaction followed by subsequent attachment of the A ring through an intramolecular aldol condensation reaction. As such, this strategy allows the synthesis of truncated englerins. Evaluation of these analogues with the A498 renal cancer cell-line suggested that the A ring of englerin is crucial to its antiproliferative activity. Moreover, evaluation of these analogues led to the identification of potent growth-inhibitors of CEM cells with GI50 values in the range 13 mu M.
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