1005000-03-2

Upstream product

• 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 

Downstream Products

• 1004999-93-2 diethyl 2,2'-((1R,2S)-2',3'-dimethoxy-1,2,3,4-tetrahydro-[1,1'-biphenyl]-1,2-diyl)diacetate 
• 872033-94-8 N-(2-((3R,3aR,3a1S,9aS)-3-hydroxy-5-methoxy-1,2,3,3a,3a1,9a-hexahydrophenanthro[4,5-bcd]furan-3a1-yl)ethyl)-N,4-dimethylbenzenesulfonamide 
• 1440947-69-2 N-(2-(3-hydroxy-5-methoxy-3,3a,3a¹,9a-tetrahydrophenanthro[4,5-bcd]furan-3a¹-yl)ethyl)-N,4-dimethylbenzenesulfonamide 
• 1440947-74-9 C₃₁H₄₃NO₅SSi 

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