184784-56-3

Upstream product

• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 18802-96-5 4-methyl-2-pentenoyl chloride 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 

Downstream Products

• 176018-91-0 (S)-3-((S)-4-Methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 184784-33-6 (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one 
• 6070-68-4 (2S,3R)-3-Isopropyl-5-oxo-pyrrolidine-2-carboxylic acid 
• 1359864-47-3 (3S)-3-(4'-methoxyphenyl)-4-methylpentanoic acid 
• 1359864-48-4 (5S)-2-diazo-5-(4'-methoxyphenyl)-6-methylheptan-3-one 
• 1421671-85-3 (+)-(3S)-3-(4-methylphenyl)-4-methylpentanoic acid 
• 1421671-86-4 (+)-(5S)-2-diazo-5-(4-methylphenyl)-6-methylheptan-3-one 
• 1421671-84-2 (3S,4S)-3-[3-(4-methylphenyl)-4-methylpentanoyl]-4-phenyloxazolidin-2-one 
• 194031-75-9 (S)-3-[(2R,3S)-2-Azido-3-(4-methoxy-2,6-dimethyl-phenyl)-4-methyl-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 194031-69-1 (S)-3-[(2S,3S)-2-Azido-3-(4-methoxy-2,6-dimethyl-phenyl)-4-methyl-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 194031-73-7 (S)-3-[(2S,3S)-2-Bromo-3-(4-methoxy-2,6-dimethyl-phenyl)-4-methyl-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 194031-79-3 (2R,3S)-2-Azido-3-(4-methoxy-2,6-dimethyl-phenyl)-4-methyl-pentanoic acid 

Relevant academic research and scientific papers

Synthetic approaches to the daucane sesquiterpene derivatives employing the intramolecular Buchner cyclisation of α-diazoketones

The use of the intramolecular Buchner cyclisation of an α-diazoketone as an approach to the synthesis of daucane sesquiterpenes is described; in particular the synthesis of the cis-fused analogue of dihydro CAF-603. The key step in the synthesis is the intramolecular Buchner cyclisation, which provides the bicyclo[5.3.0]decane framework with the required stereochemistry at the quaternary centre generated in the cyclisation. A synthetic route enabling access to an asymmetric synthesis is also outlined.

Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

The asymmetric synthesis of cis-7-methoxycalamenene 1 has been accomplished using the intramolecular Buchner reaction of α-diazoketone 7 as the key step in the synthetic route. Upon reduction of the equilibrating azulenone structure 8, the resulting azulenol 9 rearranges to dihydronaphthalene 10 containing the 6,6-membered bicyclic ring system characteristic of 1, by means of an acid-catalyzed aromatization process. Transformation of 10 to 1 is accomplished through a three-step reaction sequence.

Conjugate additions of a simple monosilylcopper reagent with use of the CuI-DMS complex: Stereoselectivities and a dramatic impact by DMS

(Chemical Equation Presented) Conjugate additions utilizing the simple monosilylcuprate reagent Li[PhMe2SiCuI] to α,β-unsaturated carbonyl compounds are described. The presence of dimethyl sulfide (DMS), either as a component originating from t

Synthesis and conformational features of topographically constrained designer chimeric amino adds: The β-isopropyl phenylalanines

All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, β-isopropylphenylalanine or β- phenylleucine, were asymmetrically synthesized in five to six steps in 20 - 25% overall yield. Computer-assisted molecular modeling revealed that the β- isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations.

Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines

All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2',6'-dimethyl-tyrosines

All four stereoisomers of the highly constrained aromatic α-amino acid β-isopropyl-2',6'-dimethyltyrosine have been asymmetrically synthesis on a large scale. A catalytic asymmetric Michael addition of an organocuprate to a chiral α,β-unsaturated acyloxazolidinone and subsequent direct or indirect stereoselective electrophilic azidation of the α-position of the resulting product was followed by hydrolysis, hydrogenation and finally deprotection of the phenol group to afford the desired amino acids. The reactions generally proceeded in good stereoselectivities (75-95% ee/de) and yields (70-90%), making these optically pure amino acids available in large scale practical for the synthesis of peptides and other studies.