116-28-9Relevant articles and documents
An improved synthetic route to huperzine A; New analogues and their inhibition of acetylcholinesterase
Kozikowski,Campiani,Aagaard,McKinney
, p. 860 - 862 (1993)
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Synthesis and biological evaluation of (±)-Z-huperzine A
Kozikowski, Alan P.,Yamada, Fumio,Tang,Hanin, Israel
, p. 6159 - 6162 (1990)
The synthesis of (±)-Z-huperzine A has been accomplished and the ability of this agent to inhibit acetylcholinesterase has been measured. The compound has an IC50 of 6 × 10-6 M, which is comparable to that of huperzine B.
Synthetic method of huperzine A
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Paragraph 0075; 0077; 0118-0121, (2019/05/15)
The invention belongs to the technical field of medicine synthesis and particularly relates to a synthetic method of huperzine A. The method includes twelve steps of reactions, 1,4-dioxaspiro[4.5]decan-8-one being a raw material, so that the chemical synthesis of the huperzine A is completed at a high total yield. The method is fewer in reaction steps, is simple in operations, has high yield, is stable in intermediates and gentle in reaction conditions, and is easy to control in reactions.
PREPARATION OF (-)-HUPERZINE A
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Paragraph 0128; 0129, (2016/06/28)
The present invention relates to a method for preparing (?)-huperzine A. The method involves: allowing a mixture of (±)-huperzine A obtained from chemical synthesis and a chiral acid to form (±)-huperzine A chiral acid salt under suitable conditions; recrystallizing the chiral acid salt from an organic solvent and basifying with an alkali to obtain optically pure (?)-huperzine A. The method is convenient to operate and suitable for industrial production. The chemical purity and optical purity of (?)-huperzine A obtained by the method are each greater than 99.5%, satisfying the requirement for raw pharmaceutical purity in the pharmaceutical industry.
Divergent total synthesis of the lycopodium alkaloids huperzine A, huperzine B, and huperzine U
Ding, Rui,Fu, Jian-Guo,Xu, Guang-Qiang,Sun, Bing-Feng,Lin, Guo-Qiang
, p. 240 - 250 (2014/01/17)
Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.