135006-48-3

Upstream product

• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 1577-22-6 5-hexenoic acid 
• 36394-07-7 5-hexenoyl chloride 

Downstream Products

• 442913-55-5 (4R,5S)-3-((R)-2-Hydroxy-hex-5-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 1101859-68-0 (4R,5S)-4-methyl-5-phenyl-3-((E)-6-phenylhex-5-enoyl)oxazolidin-2-one 
• 135006-25-6 (4R)-2,6-dimethylphenyl 2,4-dimethyl-3-hydroxyoct-7-enoate 
• 135006-50-7 (2R)-(-)-benzyl 2-methyl-5-hexenoate 
• 442913-56-6 (4R,5S)-3-((R)-2-Methoxymethoxy-hex-5-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 135006-49-4 (4R,5S)-(+)-3-((2R)-2-methyl-1-oxo-5-hexenyl)-4-methyl-5-phenyloxazolidone 

Relevant academic research and scientific papers

SmI2-promoted intra- and intermolecular C-C bond formation with chiral N-acyl oxazolidinones

The suitability of chiral oxazolidinones in the SmI2-mediated C-C bond generation between the imide functionality of an N-acyl oxazolidinone unit and an olefinic radical acceptor, in both inter- and intramolecular reactions, was investigated. It was shown that the products from an Evans asymmetric alkylation can undergo direct carbon-carbon bond formation with an acrylamide providing chiral acyclic ketones in reasonable yields. These examples represent the first transformation of such N-acyl oxazolidinones where this chiral auxiliary is removed under the conditions for ketone formation. 5-exo-trig Cyclization studies were also undertaken with the same type of substrates, providing trans-2,5-disubstituted cyclopentanones in yields of approx. 50%. However, attempts to cyclize heteroatom-containing equivalents were less rewarding.

The chemistry of cyclic vinyl ethers. 6. Total synthesis of polyether ionophore antibiotics of the calcimycin (A-23187) class

An extremely convergent (longest linear sequence, 16 steps), fully stereoselective, and potentially general synthesis of the antibiotic ionophores of the Calcimycin (A-23187) class was devised. The key steps involve a coupling reaction between the chiral nonracemic subunits dihydropyran 41 (as the α-lithio anion) and bromide 49. Subsequent acid-promoted cyclization directly produces the spirocyclic ring system found in the ionophore X-14885A (3). Alternatively, cyclopropanation of substituted vinyl ether 55 followed by acid treatment afforded the spiroketal 58 that was subsequently converted into the polyether ionophore Calcimycin (1) and also Cezomycin (2).