1353660-75-9

Upstream product

• 174729-15-8 (2S,3R)-methyl 3-(4-fluorophenyl)-2,3-dihydroxypropanoate 
• 1353660-38-4 (2S,3S)-methyl 3-azido-3-(4-fluorophenyl)-2-hydroxypropanoate 
• 1353660-46-4 (2S,3S)-methyl 3-azido-3-(4-fluorophenyl)-2-methoxypropanoate 
• 1353660-56-6 (2S,3S)-methyl 3-amino-3-(4-fluorophenyl)-2-methoxypropanoate 
• 1353660-65-7 C₃₁H₃₉FN₄O₇ 
• 96426-60-7 methyl (2E)-3-(4-fluorophenyl)-2-propenoate 

Downstream Products

• 1353660-83-9 C₃₆H₄₅FN₄O₆ 

Relevant academic research and scientific papers

Synthesis of chondramide a analogues with modified β-tyrosine and their biological evaluation

Starting from cinnamates 9, obtained by Wittig reaction or Heck coupling, the diols 17 were prepared by asymmetric dihydroxylation. This was followed by a regioselective substitution of the 3-OH group with hydrazoic acid under Mitsunobu conditions. Methylation of the 2-OH group and reduction of the azide group led to the β-tyrosine derivatives 8. Condensation with the dipeptide acid 6 furnished the tripeptide part of the chondramides. The derived acids 21 were combined with the hydroxy ester 7 to the esters 22. Cleavage of the tert-butyl groups and intramolecular lactam formation gave rise to the chondramide A analogues 2 b-k. Growth inhibition assays showed most of the analogues to be biologically active. Some of them even reach the activity of jasplakinolide. It can be concluded that the 4-position of the aryl ring in the β-tyrosine of chondramide A tolerates structural modifications quite well.