123673-81-4

Upstream product

• 38580-68-6 4-hydroxymethyl-cyclohexanone 
• 132452-43-8 4-<(phenylmethoxy)methyl>cyclohexanone 
• 96184-81-5 (+/-)-cyclohexanone-4-carboxaldehyde 
• 40242-22-6 15H-20,21-dinor-eburnamenin-14-one 
• 34963-16-1 (+/-)-(3α,16β)-desethyleburnamonine 

Relevant academic research and scientific papers

Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

A concise stereoselective total synthesis of (±)-vindeburnol and its epimer (±)-16-epi-vindeburnol is presented. This synthetic work features the utilization of Baeyer-Villiger oxidation to install different types of lactone substrate, and a sequence of a

Formal Synthesis of Bioactive Indole Alkaloids Eburnamonine, Eburnaminol, and Vindeburnol

Starting from (±)-3-acetoxyglutarimide, diastereoselective formal synthesis of indole alkaloids (±)-eburnamonine, (±)-eburnaminol, and (±)-vindeburnol have been demonstrated via a common intermediate (±)-1-hydroxy-12-tosyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one in very good overall yields. The acetoxy group from (±)-3-acetoxyglutarimide was first used to induce the diastereoselectivity and also as a latent source of ketone carbonyl group. The stereoselective eliminations, reductions, and intramolecular cyclizations were the involved key steps.

Use of 14,15-dihydro-20,21-dinoreburnamenin-14-ol for the treatment and/or prevention of serious depression and sleep/waking cycle disorders

The invention relates to a novel therapeutic use of 14,15-dihydro-20,21-dinoreburnamenin-14-ol for the treatment of serious depression in humans, particularly for the treatment of a patients resistant to conventional anti-depressant treatments and for treatment of sleep/waking cycle disorders.

Total synthesis of (±)-deethyleburnamonine and vindeburnol (RU 24722) with the corresponding nitriles as starting material

Cyclisation occurred during base treatment of cis-nitrile (5). The resulting new imine (6) was converted into the therapeutically important deethyleburnamonine (4). Total synthesis of vindeburnol (RU 24722) (3), another important drug, was achieved in one step starting from the trans- nitrile (9).

METHOD OF TREATING DEPRESSION WITH OPTICALLY ACTIVE ISOMERS OF 20,21-DINOREBURNAMENINES

A compound selected from the group consisting of optically active isomers of a racemic compound of the formula STR1 wherein the 3-hydrogen and 16-hydrogen are trans and STR2 is selected from the group consisting of STR3 with the--OH being α or β and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressant activity and an affinity for alpha 2 adrenergic receptors,