409087-87-2

Upstream product

• 591-80-0 pent-4-enoic acid 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 39716-58-0 pent-4-enoyl chloride 

Downstream Products

• 637767-34-1 (1R,2R,5S,6S,7S)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid (1S,2R)-2-pent-4-enoylamino-1-phenyl-propyl ester 
• 637767-32-9 (1S,2S,5R,6R,7R)-2-(Allyl-benzyl-carbamoyl)-3-(4-methoxy-benzyl)-4-oxo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid (1S,2R)-2-pent-4-enoylamino-1-phenyl-propyl ester 

Relevant academic research and scientific papers

Synthesis of chiral 1,5-disubstituted pyrrolidinones via electrophile-induced cyclization of 2-(3-butenyl)oxazolines derived from (1R,2S)- and (1S,2R)-norephedrine

Starting from (1R,2S)- and (1S,2R)-norephedrine, enantiomers of the corresponding 2-(3-butenyl)oxazolines were prepared in a two-step process. The cyclization of the intermediate alkenylamides with phenylselenyl bromide afforded cyclic imidates instead of the expected pyrrolidinones. The electrophile-induced cyclizations of 2-alkenyloxazolines with bromine or iodine produced diastereomeric mixtures of chiral 1,5-disubstituted pyrrolidinones. The ring closure of the all-cis (1R,2S,5R)-diastereomer 7 with NaH resulted in the tetrahydropyrrolo[2,1-b]oxazol-5-one derivative 18, which was alternatively prepared by the cyclocondensation of (1R,2S)-norephedrine with levulinic acid.

Stereochemical Control of Skeletal Diversity

(Equation presented) Substrates having appendages that pre-encode skeletal information (σ-elements) can be converted into products having distinct skeletons using a common set of reaction conditions. The sequential use of the Ugi 4CC-IMDA reaction, followed by allylation, hydrolysis, and acylation of a chiral amino alcohol appendage (σ-element), leads to substrates for a ROM/RCM or RCM reaction. The stereochemistry of the a-element and not its constitution controls the outcome of the pathway selected. This work illustrates the potential of linking stereochemical control to the challenging problem of skeletal diversity.

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright