22169-18-2

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 51714-24-0 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 1699-51-0 laudanosine 
• 102922-34-9 2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 2258-42-6 formyl acetic anhydride 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 41183-00-0 7-benzyloxy-1-(3,4-dimethoxy-benzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling

A fully regio- and diastereoselective electrochemical 4a-2′-coupling of a 3′,4′,5′-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (-)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.

The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid

The non-phenolic coupling reaction of benzyltetrahydroisoquinolines (laudanosine derivatives) by using a hypervalent iodine(III) reagent is described. In general, chemical oxidation of laudanosine gives glaucine. In contrast to general chemical oxidizing reagent systems, the novel use of reagent combination of phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) afforded morphinandienone alkaloids in excellent yields. In order to achieve the coupling reaction with simple reaction procedure, the use of HPA supported on silica gel instead of HPA was demonstrated and sufficient yield was exerted again. The present reagent system, PIFA/HPA, was also applied to the oxidation of other non-phenolic benzyltetrahydroisoquinolines and the high yield conversion to morphinandienones was accomplished.

Electrochemical Oxidation of Morphinandienones

The (+/-)-morphinandienones, O-methylflavinantine, O-benzyllaudanine, and O-methylflavinine, were synthesized by electrochemical oxidation of laudanosine, O-benzylpalladine, and norlaudanosine.With use of acetonitrile containing fluoroboric acid as solven