Journal
ORGANIC LETTERS
Volume 21, Issue 8, Pages 2952-2956Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01042
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- Recruitment Program of Global Experts (1000 Talents Plan)
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The first asymmetric total syntheses of tuberostemoamide, sessilifoliamide A, and their epimers have been accomplished via the common intermediate ethylstemoamide. The stereochemistry control relationship at C8/C9/C10 of ethylstemoamide is clearly revealed for the first time, and a subtle difference of substituent at the C10 position between stemoamide and ethylstemoamide (Me vs Et) drastically changes the stereoselectivity, which is significantly valuable for syntheses of ethylstemoamide structurally related Stemona alkaloids. Biological studies reveal that the activities of each epimer show a significant difference. 11,13-Bis-epi-sessilifoliamide A is expected to be a selective and reversible BChE inhibitor for the treatment of neuro-degenerative diseases, and sessilifoliamide A may be a part of the anti-inflammatory substances in Stemonaceae plants.
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