期刊
CHEMICAL SCIENCE
卷 2, 期 2, 页码 308-311出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00577k
关键词
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资金
- NIHGMS [R01 GM078201]
- Eli Lilly
- Bristol-Myers Squibb
- Princeton University
- Eisai
- NSF
- NIH [NIH-F32-CA-091635-01]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM078201] Funding Source: NIH RePORTER
A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation-cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.
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