Asymmetric Total Syntheses and Biological Studies of Tuberostemoamide and Sessilifoliamide A

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...

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Published inOrganic letters Vol. 21; no. 8; pp. 2952 - 2956
Main Authors Hou, Yongsheng, Shi, Tao, Yang, Yuhang, Fan, Xiaohong, Chen, Jinhong, Cao, Fei, Wang, Zhen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.04.2019
Amer Chemical Soc
Subjects
alkaloids
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
cholinesterase
neurodegenerative diseases
Physical Sciences
Science & Technology
Stemona
stereochemistry
stereoselectivity
ALKALOIDS
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Summary: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 neurodegenerative diseases, and sessilifoliamide A may be a part of the anti-inflammatory substances in Stemonaceae plants.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.9b01042