872033-94-8

Upstream product

• 1440947-74-9 C₃₁H₄₃NO₅SSi 
• 1004999-92-1 C₂₃H₃₄O₅Si 
• 1004999-93-2 diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate 
• 1004999-94-3 (2R,3R)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1005000-06-5 diethyl 2,2'-((1S,4R,4aR,9bS)-4-((tert-butyldimethylsilyl)oxy)-6-methoxy-1,2,3,4,4a,9bhexahydrodibenzo[b,d]furan-1,9b-diyl)diacetate 
• 1005000-04-3 diethyl 2,2'-((1S,4R,4aR,9bS)-4-hydroxy-6-methoxy-1,2,3,4,4a,9b-hexahydrodibenzo[b,d]furan-1,9bdiyl)diacetate 
• 1005000-03-2 ethyl 2-((2S,5R)-5-hydroxy-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate 
• 1005000-02-1 ethyl 2-((2S,5R)-5-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-yl)acetate 
• 1005000-01-0 (2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2',3'-dimethoxy-2,3,4,5-tetrahydro-[1,1'-biphenyl]-2-ol 
• 1005000-00-9 tert-butyl(((2R,3R)-2',3'-dimethoxy-2-((4-methoxybenzyl)oxy)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-3-yl)oxy)dimethylsilane 
• 1004999-95-4 (5R,6S)-5-((tert-butyldimethylsilyl)oxy)-6-((4-methoxybenzyl)oxy)cyclohex-1-en-1-yltrifluoromethanesulfonate 
• 1440947-46-5 (5R,6S)-5-((tert-butyldimethylsilyl)oxy)-6-((4-methoxybenzyl)oxy)cyclohex-2-enone 
• 144318-25-2 4,N-Dimethyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of (-)-morphine: Application of sequential claisen/claisen rearrangement of an allylic vicinal diol

A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product.

Formal synthesis of (-)-morphine from d-glucal based on the cascade Claisen rearrangement

The formal synthesis of (-)-morphine is described. The C-ring in morphine was prepared in an optically pure form from d-glucal using Ferrier's carbocyclization reaction, and the vicinal tertiary and quaternary stereocenters in the C-ring were stereoselect

Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine

The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b → (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials.