870137-24-9

Upstream product

• 912341-76-5 (2S,3R)-3-(4-Benzyloxy-3-{(R)-1-[(S)-((S)-2-benzyloxycarbonylamino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-prop-2-ynyloxy}-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid benzyl ester 
• 870137-16-9 {[(2S,3S)-3-ethynyl-3-methyl-1-(2-nitrobenzenesulfonyl)-aziridine-2-carbonyl]amino}acetic acid tert-butyl ester 
• 870137-17-0 (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester 
• 870137-23-8 (2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester 
• 870137-15-8 (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester 

Relevant academic research and scientific papers

Evolution of the total syntheses of ustiloxin natural products and their analogues

Ustiloxins A-F are antimitotic heterodetic cyclopeptides containing a 13-membered cyclic core structure with a synthetically challenging chiral tertiary alkyl-aryl ether linkage. The first total synthesis of ustiloxin D was achieved in 31 linear steps using an SNAr reaction. An NOE study of this synthetic product showed that ustiloxin D existed as a single atropisomer. Subsequently, highly concise and convergent syntheses of ustiloxins D and F were developed by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequence of 15 steps. The approach was further optimized to achieve a better macrolactamization strategy. Ustiloxins D, F, and eight analogues (14-MeO-ustiloxin D, four analogues with different amino acid residues at the C-6 position, and three (9R,10S)-epi-ustiloxin analogues) were prepared via the second-generation route. Evaluation of these compounds as inhibitors of tubulin polymerization demonstrated that variation at the C-6 position is tolerated to a certain extent. In contrast, the S configuration of the C-9 methylamino group and a free phenolic hydroxyl group are essential for inhibition of tubulin polymerization.

Total synthesis and biological evaluation of ustiloxin natural products and two analogs

Synthetic investigations of ustiloxin natural products are described. The first total synthesis of ustiloxin F was completed in 15 steps via ethynyl aziridine ring-opening by a phenol derivative. The results of biological tests of synthetic ustiloxins D a