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A Concise Total Synthesis of (±)-Mesembrine
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Publication Year
2018-06-01
Publisher
Georg Thieme Verlag
Citation
Synlett, Vol.29, pp.1203-1206
Keyword
3a-(aryl)octahydro-indoleallylic transferbenzylic quaternary stereogenic centermesembrinenatural productstotal synthesis
All Science Classification Codes (ASJC)
Organic Chemistry
Abstract
A concise total synthesis of (±)-mesembrine has been successfully accomplished in seven steps and 24% overall yield from commercially available 3-ethoxy-2-cyclohexen-1-one. Central to the assembly of the skeleton of mesembrine are a Johnson-Claisen rearrangement for the formation of the benzylic quaternary stereocenter and direct allylic oxidation to generate the substrate for the amidation/transannular aza-conjugate addition reaction.
Language
eng
URI
https://dspace.ajou.ac.kr/dev/handle/2018.oak/30105
DOI
https://doi.org/10.1055/s-0036-1591547
Fulltext

Type
Article
Funding
This work was supported by the Basic Science Research Program from the National Research Foundation of Korea (NRF-2016R1C1B1008816) funded by the Ministry of Education and the 2017 Research Fund of the Catholic University of Korea.Noaitnal Reseacrh Foundoaitn of Koera N(RF-2016R1C1B1008816)
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Kim, Hyoungsu Image
Kim, Hyoungsu김형수
Division of Pharmacy Sciences
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