182486-25-5

Upstream product

• 86302-43-4 (tert-Butoxycarbonylmethylene)triphenylphosphorane 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 179093-50-6 (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid 
• 178977-57-6 tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate 
• 182486-31-3 (2E,7E)-(5R,6R)-5-Hydroxy-6-methyl-8-phenyl-octa-2,7-dienoic acid tert-butyl ester 
• 182699-64-5 (2R)-methyl 2-methyl-2-(trans-styryl)acetate 
• 182699-58-7 (E)-2-methyl-4-phenylbut-3-enal 
• 182486-23-3 (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid allyl ester 
• 33599-85-8 (E)-2-methyl-4-phenyl-3-butenoic acid methyl ester 
• 91083-82-8 (E)-methyl 4-phenylbut-3-enoate 
• 178977-50-9 (4S,5S)-4-Hydroxy-5-phenylethynyl-dihydro-furan-2-one 
• 179093-49-3 (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid 
• 1054658-49-9 2,2-Dimethyl-propionic acid (E)-(3S,4S)-4-acetoxy-6-phenyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl ester 

Downstream Products

• 124689-64-1 cryptophycin C 
• 124689-65-2 cryptophycin-1 

Relevant academic research and scientific papers

Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae

A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio

Total synthesis of cryptophycins via a chemoenzymatic approach

A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

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.