612492-53-2

Upstream product

• 612492-51-0 N-Fmoc-Tyr(O-Me)-(N-Me)Ala-OH 
• 77128-72-4 N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine 
• 916912-48-6 (S)-2-{[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-propionic acid benzyl ester 

Downstream Products

• 916913-03-6 C₆₃H₈₉N₅O₁₂Si 
• 916913-02-5 C₆₄H₉₁N₅O₁₂Si 
• 916913-01-4 C₆₄H₉₁N₅O₁₂Si 
• 916912-49-7 C₆₇H₉₅N₅O₁₂SSi 
• 350791-64-9 (-)-apratoxin A 
• 612492-54-3 C₆₅H₉₃N₅O₁₂Si 

Relevant academic research and scientific papers

Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities

A novel total synthesis of apratoxin A is described, with key steps including the assembly of its ketide segment through a D-proline-catalyzed direct aldol reaction and Oppolzer's anti aldol reaction and the preparation of its thiazoline unit in a biomimetic synthesis. An oxazoline analogue of apratoxin A has also been elaborated by a similar approach. This compound has a potency against HeLa cell proliferation only slightly lower than that of apratoxin A, whilst a C(40)-demethylated oxazoline analogue of apratoxin A displays a much lower cytotoxicity and the C(37)-epimer and C(37) demethylation prod uct of this new analogue are inactive. These results suggest that the two methyl groups at C(37) and C(40) and the stereochemistry at C(37) are essential for the potent cellular activity of the oxazoline analogue of apratoxin A. Further biological analysis revealed that both synthetic apratoxin A and its oxazoline analogue inhibited cell proliferation by causing cell cycle arrest in the G1 phase.

Synthesis of an Oxazoline Analogue of Apratoxin A

Equation presented. Michael addition of Me2Cu(CN)Li2 to α,β-unsaturated lactone 7 derived from β-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 wi