191417-77-3

Upstream product

• 213614-10-9 N-[2-(5-methoxy-3-oxo-3,8-dihydro-3aH-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide 
• 115-37-7 thebaine 
• 2297-65-6 benzenesulfonyl bromide 
• 191417-70-6 2-((4aR,10aS)-8-Chloro-5,6-dimethoxy-1,9,10,10a-tetrahydro-2H-phenanthren-4a-yl)-N,N-dimethyl-acetamide 
• 191417-74-0 N-[2-((1aR,3aR,9bS,9cS)-6-Chloro-8,9-dimethoxy-1a,3,3a,4,5,9c-hexahydro-2H-1-oxa-cyclopropa[c]phenanthren-9b-yl)-ethyl]-N-methyl-benzenesulfonamide 
• 191417-75-1 N-[2-((3R,3aR,9aR,9bS)-7-Chloro-3-hydroxy-5-methoxy-1,3,3a,8,9,9a-hexahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-N-methyl-benzenesulfonamide 
• 191417-72-8 N-[2-((4aR,10aS)-8-Chloro-5,6-dimethoxy-1,9,10,10a-tetrahydro-2H-phenanthren-4a-yl)-ethyl]-N-methyl-benzenesulfonamide 
• 191417-71-7 2-((4aR,10aS)-8-Chloro-5,6-dimethoxy-1,9,10,10a-tetrahydro-2H-phenanthren-4a-yl)-ethanol 
• 239123-50-3 (R)-8-Chloro-5,6-dimethoxy-1,2,3,9,10,10a-hexahydro-phenanthren-3-ol 
• 207731-96-2 8-chloro-5,6-dimethoxy-1,9,10,10a-tetrahydrophenanthren-3(2H)-one 

Downstream Products

• 186351-18-8 1,2,3,3a(R),8,9,9a(R),9b(S)-octahydro-5-methoxy-9b-[2-[N-methyl-N-(phenylsulfonyl)amino]ethyl]-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan 
• 125-29-1 Hydrocodone 
• 207731-95-1 1,2,3,3a(R),9a(R),9b(S)-hexahydro-5-methoxy-9b-[2-[N-methyl-N-(phenylsulfonyl)amino]ethyl]-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan 

Relevant academic research and scientific papers

New ventures in the construction of complex heterocycles: Synthesis of morphine and hasubanan alkaloids

Synthetic approaches to morphine and hasubanan alkaloids involving novel reactions for the formation of their dihydrobenzofuran, piperidine and pyrrolidine ring, respectively, are described. The importance of conformational constraints for the success of these reactions is demonstrated. The syntheses of new dioxepanes, diazepanes, dithiocanes, triazenes and dioxonanes are also reported.

Synthesis of enantiomerically pure morphine alkaloids: The hydrophenanthrene route

A concise, linear, total synthesis of (-)-dihydrocodeinone - a close synthetic precursor of (-)-codeine and (-)-morphine - has been achieved. The carbocyclic core of the alkaloid was provided in the form of a phenanthrenone, which was resolved by chromatography on cellulose triacetate. A cuprate conjugate addition was used to establish the crucial benzylic quaternary stereocenter and to introduce the C2-side chain. Dimeric byproducts provide evidence for a single electron transfer (SET) mechanism. Unusual S(N)2 and radical cyclizations were employed for the formation of the dihydrobenzofuran and the piperidine ring, respectively.