期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 28, 页码 12027-12033出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04914
关键词
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资金
- Division of Chemistry (CHE), National Science Foundation [NSF/CHE-1834750]
- Division of Materials Research (DMR), National Science Foundation [NSF/CHE-1834750]
- U.S. DOE [DE-AC02-06CH11357]
- University of Chicago
- National Institutes of Health [NIH R01-124295A]
Among defensive alkaloids isolated from ladybugs, the heterodimeric member chilocorine C possesses an alluring monomeric unit that combines quinolizidine and indolizidine substructures. Indeed, the overall stereochemical disposition of its ring fusions is distinct from those of related natural products. Herein we show that a carefully orchestrated sequence with several chemoselective transformations, including a designed cascade that accomplishes nine distinct chemical reactions in one-pot, can smoothly forge that domain and ultimately enable a 15-step, 11-pot enantiospecific synthesis of the natural product. Mechanistic studies, density functional theory calculations, and the delineation of several other unsuccessful approaches highlight its unique elements.
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