870137-17-0

Upstream product

• 870137-21-6 (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester 
• 821006-10-4 (4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester 
• 821006-11-5 (4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester 
• 1013210-17-7 (2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 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 
• 870137-24-9 (2S,3R)-3-(3-{(R)-1-[(S)-((S)-2-Amino-propionylamino)-(tert-butoxycarbonylmethyl-carbamoyl)-methyl]-1-methyl-propoxy}-4-hydroxy-phenyl)-2-(tert-butoxycarbonyl-methyl-amino)-3-hydroxy-propionic acid 
• 870137-22-7 (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-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 

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.

A convergent total synthesis of ustiloxin D via an unprecedented copper-catalyzed ethynyl aziridine ring-opening by phenol derivatives

(Chemical Equation Presented) The ustiloxins are a family of heterodetic cyclopeptides that have been isolated from the water extracts of false smut balls on the panicles of rice plants caused by the fungus Ustilaginoidea virens. A concise total synthesis of ustiloxin D has been achieved via an unprecedented ethynyl aziridine ring-opening of phenol derivatives. The longest linear sequence of the synthesis is 15 steps from commercially available compounds.