(+)-huperzine A

Base Information

• Chemical Name: (+)-huperzine A
• CAS No.: 130791-77-4
• Molecular Formula: C₁₅H₁₈N₂O
• Molecular Weight: 242.321
• Mol file: 130791-77-4.mol

Synonyms:(+)-huperzine A

Chemical Property of (+)-huperzine A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-huperzine A

There total 66 articles about (+)-huperzine A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate (185741-46-2) → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate; With trimethylsilyl iodide; In chloroform; for 6h; Reflux; Inert atmosphere;

With methanol; In chloroform; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ol9022408

Reference yield: 74.0%

(-)-huperzine A 2,3-dibenzoyl-D-tartaric acid salt → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In water; for 1h; pH=9 - 9.3;

Reference yield: 60.0%

C16H16N2O2 → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 80 ℃; for 36h;

upstream raw materials:

(1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraene-1-carboxylic acid

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate

(5S,9R)-methyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cycloocta[b]pyridine-5-carboxylate

(1S,9S)-5-Methoxy-11-methylene-13-oxo-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid methyl ester

Downstream raw materials:

(5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one

natural Huperzine A

(+)-huperzine A

N,N-dicyclohexylurea

Refernces

• 1、 -. "METHODS OF RESOLVING RACEMIC MIXTURE TO OBTAIN (-)-HUPERZINE A". Page/Page column 10. . Retrieved 2016/04/26.
• 2、 White, James D.,Li, Yang,Kim, Jungchul,Terinek, Miroslav. "Cyclobutane Synthesis and Fragmentation. A Cascade Route to the Lycopodium Alkaloid (-)-Huperzine A". . p. 11806 - 11817. Retrieved 2015/12/11.