1440947-69-2

Upstream product

• 259209-17-1 [2-hydroxy-3-(methyloxy)phenyl]boronic acid 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 1440947-88-5 C₂₃H₃₆O₅Si 
• 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 
• 481634-93-9 5-methoxy-9b-(2-methylaminoethyl)-3,3a,9a,9b-tetrahydrophenanthro[4,5-bcd]furan-3-ol 

Relevant academic research and scientific papers

Total Synthesis of Codeine

In this paper, a new strategy towards the synthesis of codeine and morphine is reported. This new approach features a cascade cyclization to construct the dihydrofuran ring, and an intramolecular palladium catalyzed C-H olefination of unactivated aliphatic alkene to install the morphinan ring system.

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.