178977-50-9

Upstream product

• 4440-01-1 lithium phenylacetylide 
• 536-74-3 phenylacetylene 

Downstream Products

• 178977-58-7 (4S,5S)-5-Phenylethynyl-4-(tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 245125-92-2 tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 1054658-49-9 2,2-Dimethyl-propionic acid (E)-(3S,4S)-4-acetoxy-6-phenyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl ester 
• 178977-62-3 (2E,7E)-(5S,6R)-6-Methyl-8-phenyl-5-(tetrahydro-pyran-2-yloxy)-octa-2,7-dienoic acid tert-butyl ester 
• 178977-60-1 2,2-Dimethyl-propionic acid (E)-(3S,4R)-4-methyl-6-phenyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl ester 
• 178977-55-4 (3S,4S)-2,2-dimethylpropionic acid 4-acetoxy-3-hydroxy-6-phenylhex-5(E)-enyl ester 
• 178977-61-2 (E)-(3S,4R)-4-Methyl-6-phenyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-en-1-ol 
• 178977-56-5 (3S,4S)-2,2-dimethylpropionic acid 3-hydroxy-4-methyl-6-phenylhex-5(E)-enyl ester 
• 178977-57-6 tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate 
• 182486-25-5 tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 
• 124689-64-1 cryptophycin C 
• 155645-51-5 Cryptophycin 4 
• 178977-54-3 (3S,4S)-3-(tetrahydropyran-2-yloxy)-6-phenylhex-5(E)-ene-1,4-diol 

Relevant academic research and scientific papers

Total synthesis of cryptophycins and their 16-(3-phenylacryloyl) derivatives

Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A,B, C, and D.

Synthesis and in vitro cytotoxicity of cryptophycins and related analogs

Several members of the Cryptophycin family were synthesised using a straightforward convergent approach. The proposed synthetic route was used to prepare novel analogs of Cryptophycins A and B in which the benzylic epoxide moiety was replaced by alternate electrophilic functions. The effect of these modifications on cytotoxic activity was determined on several tumor cell lines.