64474-08-4

Upstream product

• 24724-18-3 10,11-Dibromo-1-undecanol 
• 80289-83-4 7-methyl-3-oxo-2-(10-oxo-undecyl)-oct-6-enoic acid ethyl ester 
• 57689-12-0 17-methyl-octadec-16-ene-2,13-dione 
• 57689-14-2 4,15-dioxo-hexadecanal 
• 35345-72-3 11-hydroxyundecan-2-one 
• 80289-80-1 11-bromoundecan-2-one 
• 112-43-6 10-Undecen-1-ol 
• 2774-84-7 undec-10-yn-1-ol 
• 57689-15-3 16-hydroxy-17-nitro-octadecane-2,13-dione 
• 5227-24-7 12-((2R,6S)-5-Hydroxy-6-methyl-piperidin-2-yl)-dodecan-2-one 

Downstream Products

• 5227-24-7 3 β epi-3 cassine 

Relevant academic research and scientific papers

Asymmetric synthesis of (+)-iso-6-cassine via stereoselective intramolecular amidomercuration

The first asymmetric synthesis of (+)-iso-6-cassine is described. Lipase-catalyzed resolution, enantioselective Overman rearrangement, and diastereoselective intramolecular amidomercuration were used for the installation of the three stereocenters in (+)-

Spectamines A and B, possible inhibitors of superoxide anion production of macrophages from Cassia spectabilis

Two novel piperidine alkaloids were isolated from an African legume, Cassia spectabilis, and identified as the O-benzoyl (1, named spectamine A) and O-acetyl (2, named spectamine B) derivatives of (+)-iso-6-cassine (3). The absolute configurations of 1-3 were established to be (2R,3R,6R) using the modified Mosher's method. Compound (1) inhibited the superoxide anion production of macrophages, while it did not quench the superoxide anion which is produced by xanthine oxidase at a concentration of 25 μM.

Recherches sur la synthese totale des alcaloides appatrenant a la serie de la carpaine et de la cassine. VII. Synthese totale de la (+/-) cassine

11-Bromoundecan-2-one 6 was prepared in four steps from the commercially available undec-10-en-1-ol 3, and was used to alkylate ethyl 7-methyl-3-oxooct-6-enoate 9.The resulting intermediate was hydrolysed and decarboxylated to give the diketoolefin 11.Ozonolysis of the latter yielded the diketoaldehyde 16, wich was subjected next to condensation with nitroethane in alkaline conditions, followed by catalytic hydrogenation and cyclisation to give a ca. 50/50 mixture of 3-r-hydroxy-6-c (11-oxododecyl)-2-c-methylpiperidine and (+/-)3-epi-cassine. Another route to the key intemediate 11 was also studied, in wich 1,8-dibromooctane 13 was used to alkylate the enolates of ethyl acetoacetate and ethyl 7-methyl-3-oxooct-6-enoate, giving presumably of the olefinic diketodiester 15.Hydrolysis and decarboxylation of the crude reaction product, using aqueous baryum hydroxide, gave the desired compound 11 in an overall yield of 17 percent with respect to 1,8-dibromooctane 13.