75468-48-3

Upstream product

• 2216-51-5 (-)-menthol 
• 16832-20-5 (1R,2S,5R)-menthol bromoacetate 
• 603-35-0 triphenylphosphine 

Downstream Products

• 155339-64-3 (L)-menthyl N-benzyl-N-(t-butyloxycarbonyl)-5-amino-2E-pentenoate 
• 75468-42-7 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(triphenylphosphoranylidene)acetate 
• 1082984-76-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(triphenylphosphoranylidene)propanoate 
• 1174764-19-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-(tert-butoxycarbonylamino)-2-methyl-5-phenylpent-2-enoate 
• 125812-33-1 Buta-2,3-dienoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 87655-99-0 (3aS,6aR,7R,7aR)-2,2-Dimethyl-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalene-7-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 87726-08-7 Menthyl (3aα,6aβ,7α,7aα)-2,3,3a,5,6,6a,7,7a-Octahydro-2,2-dimethyl-1H-cyclopentapentalene-7-carboxylate 
• 87681-11-6 N,N'-Bis<(2,2,2-trichloroethoxy)carbonyl>-7-<(E)-6-(carbomenthoxy)-3,3-dimethylhex-5-enylidene>-2,3-diazabicyclo<2.2.1>heptane 
• 87655-97-8 7-<(E)-6-(carbomenthoxy)-3,3-dimethylhex-5-enylidene>-2,3-diazabicyclo<2.2.1>hept-2-ene 
• 87655-96-7 6-<(-)-(E)-5-(Carbomenthyloxy)-2,2-dimethyl-4-pentenyl>fulvene 
• 87655-95-6 (l)-(-)-Menthyl (E)-7-Oxo-5,5-dimethylhept-2-enoate 
• 155339-59-6 (L)-menthyl 1-carboethoxy-3-<<2-methoxymethyloxy>ethyl>-3-nitro-4-piperidine acetate 
• 155339-61-0 (L)-menthyl 1-carboethoxy-3-<2-(2-nitrophenylseleno)ethyl>-3-nitro-4-piperidine acetate 

Relevant academic research and scientific papers

Solvent-Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles

A solvent-controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N-aryl-α,β-unsaturated nitrones and electron-deficient allene starting materials. These reactions proceed smoothly under mild metal-free conditions affording a range of two types of skeletally distinct indole-based heterocycles in high yield and diastereoselectivity. These transformations demonstrate the use of a bifurcated cascade process that hinges on the ring-opening event of a benzazepine intermediate for the synthesis of skeletally diverse heterocyclic products and rapid access to biologically-significant, indole-based structures.

Synthesis and structure-activity relationship studies of novel tubulysin U analogues-effect on cytotoxicity of structural variations in the tubuvaline fragment

Tubulysins are cytotoxic natural products with promising anti-cancer properties, originally isolated from myxobacterial cultures. Structurally, tubulysins are tetrapeptides, incorporating three unusual (Mep, Tuv and Tup) and one proteinogenic amino acid (Ile). Here we describe the synthesis and structure-activity relationship studies of novel tubulysin U and V analogues, with variations in the central Tuv fragment, which is known to be of paramount importance for tubulysins' potency and hence cytotoxicity, but has seldom been modified in previous studies. Specifically, we replaced the natural iso-propyl and acetoxy functionalities with other structurally related groups. In general, the new analogues showed much lower potency relative to native tubulysin U. However, one of the synthetic analogues (1f) having a MOM function replacing the acetyl group exhibited a 22 nM IC50 on the HT-29 cell line which is comparable to the IC50 displayed by tubulysin U (3.8 nM). Furthermore, the synthetic methodology reported herein was found to be flexible enough to deliver different core-modified tubulysin analogues and hence may be regarded as a scalable and convenient strategy for the chemical generation of novel tubulysin analogues.