691012-69-8

Upstream product

• 312328-77-1 (1S,2R,5S)-1-((R)-1-Bromo-3-trimethylsilanyl-prop-2-ynyl)-2-(tert-butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hexane 
• 312328-76-0 (S)-1-[(1S,2R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-6-oxa-bicyclo[3.1.0]hex-1-yl]-3-trimethylsilanyl-prop-2-yn-1-ol 
• 312328-73-7 (2S,3R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylethynyl-1-oxa-spiro[2.4]heptan-4-one 
• 312328-78-2 (1S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[3-trimethylsilanyl-prop-2-yn-(E)-ylidene]-cyclopentanol 
• 312328-75-9 (R)-1-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-1-enyl]-3-trimethylsilanyl-prop-2-yn-1-ol 
• 691012-79-0 5-(tert-butyl-dimethyl-silanyloxy)-cyclopent-1-enecarbaldehyde 
• 691012-80-3 (2S,3R,4S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2-trimethylsilanylethynyl-1-oxa-spiro[2.4]heptan-4-ol 

Downstream Products

• 691012-87-0 (R)-3-{2-Chloro-3-[(R)-1-((1S,5R)-2-ethynyl-1,5-dihydroxy-cyclopent-2-enyl)-prop-2-ynyloxy]-4-methoxy-phenyl}-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 

Relevant academic research and scientific papers

Convergent approach to the maduropeptin chromophore: Aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzannulation.