Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B
Document Type
Article
Publication Date
8-1-2022
Abstract
A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (+/-)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.
Keywords
Ficus schwarzii, Schwarzinicine, Phenethylamine, Alkaloid, Synthesis, Vasorelaxation
Divisions
CHEMISTRY
Funders
MOHE Malaysia (Grant No: FRGS/1/2017/STG01/UNIM/02/3 & FRGS/1/2017/SKK10/UNIM/01/1),Malaysia Toray Science Foundation (Grant No: TML-CA/17.195(17/G62))
Publication Title
Natural Product Research
Volume
36
Issue
15
Publisher
Taylor & Francis
Publisher Location
2-4 PARK SQUARE, MILTON PARK, ABINGDON OR14 4RN, OXON, ENGLAND