期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 20, 页码 6483-6492出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03404
关键词
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资金
- National Science Foundation [CHE-0955864, CHE-1464898]
- Bristol-Myers Squibb
- Dreyfus Foundation
- UCLA Gold Shield Alumnae
- University of California, Los Angeles
- NIH-NIGMS [F31-GM113642, F31-GM117945, F31-GM121016]
- National Science Foundation GRFP [DGE-1144087]
- UCLA Graduate Division
- NSF [CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464898] Funding Source: National Science Foundation
The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2(S)-cathafoline, (+)-akuammiline, and (-)-psi-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-psi-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof.
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