Stereoselective synthesis of a dibenzo[a,g]quinolizine analog of 18-hydroxyepialloyohimban was written by Belleau, B.;Puranen, J.. And the article was included in Canadian Journal of Chemistry in 1965.Quality Control of Decahydroisoquinoline hydrochloride This article mentions the following:
Starting from cis-4-cyclohexenedicarboxylic acid anhydride, a stereoselective synthesis of cis-4-tetrahydrohomophthalic acid (I) is described. The synthesis involves selective reduction to Δ4-tetrahydrophthalide and reaction of the latter with cyanide to give mainly the cis-nitrile acid in good yield. Alkaline hydrolysis leads to the cis-homodiacid, which was characterized as its corresponding anhydride. The nitrile acid intermediate could be transformed to stereoisomeric decahydroisoquinolines. Bromolactonization of the cis-diacid I afforded the bromo-γ-lactone which underwent hydrogenolysis to the already described γ-lactone homoacid intermediate in good yield. Reduction with NaBH4 gave tetrahydroisoquinoline lactone which on heating gave the two isomeric lactams. One of them was identical to a lactam already obtained by a different route. The other one was reduced to the tetracyclic base. The corresponding trimethoxybenzoic acid ester was prepared and tested for reserpine-like activity. It was found to be inactive. In the experiment, the researchers used many compounds, for example, Decahydroisoquinoline hydrochloride (cas: 90949-02-3Quality Control of Decahydroisoquinoline hydrochloride).
Decahydroisoquinoline hydrochloride (cas: 90949-02-3) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Quality Control of Decahydroisoquinoline hydrochloride
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem