204004-79-5

Upstream product

• 103-63-9 1-phenyl-2-bromoethane 
• 6926-44-9 phenethyl azide 
• 182952-48-3 (5S,6R)-1-(2-Azidoethyl)-5,6-dihydroxycyclohexa-1,3-diene 

Downstream Products

• 204004-80-8 (1R,6S)-2-(2-Azido-ethyl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-cyclohex-2-enol 
• 204004-83-1 N-(2-{(5S,6R)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-[((2E,4E)-hexa-2,4-dienyl)oxy]-cyclohex-1-enyl}-ethyl)-acetamide 
• 204004-81-9 {(1S,2R)-3-(2-Azido-ethyl)-2-[((2E,4E)-hexa-2,4-dienyl)oxy]-cyclohex-3-enyloxy}-dimethyl-(1,1,2-trimethyl-propyl)-silane 
• 204004-82-0 2-{(5S,6R)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-[((2E,4E)-hexa-2,4-dienyl)oxy]-cyclohex-1-enyl}-ethylamine 

Relevant academic research and scientific papers

Advanced intramolecular diels-alder study toward the synthesis of (-)- morphine: Structure correction of a previously reported Diels-Alder product

A tricyclic ring system 18 containing all 5 chiral centers of the natural (-)-morphine skeleton has been synthesized in 9 steps. cis-Dienediol 11 was produced by a batch microbial dihydroxylation of (2-azidoethyl)benzene with the E. coli strain JM109(pDTG601). The key step in the synthesis was a thermal [4+2] intramolecular Diels-Alder cycloaddition of triene 16 which afforded the tricyclic adduct 17 in 62% yield. After deprotection, the absolute stereochemistry of the alcohol 18 was determined by X-ray crystallographic analysis. The previously reported Diels-Alder adduct 4a was deprotected and the absolute stereochemistry of the free alcohol was assigned by X-ray crystallography to have the structure 4c. This finding therefore constitutes the correction of the structure for 4a.