247058-11-3

Upstream product

• 131744-19-9 (4S)-4-benzyl-1,3-oxazolidine-2-thione 
• 178327-16-7 C₄H₇CO₂COC₄H₉ 
• 591-80-0 pent-4-enoic acid 

Downstream Products

• 318488-32-3 (E)-(2S,3R)-2-Allyl-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one 
• 1309575-59-4 (4S)-4-benzyl-3-((2R)-2-(2-methyl-1,3-dioxolan-2-yl)pent-4-enoyl)oxazolidine-2-thione 
• 318488-37-8 [3(2S,4R),4S]-3-(2-allyl-3-hydroxy-4-methylpent-4-enoyl)-4-benzyloxazolidin-2-thione 

Relevant academic research and scientific papers

Total synthesis of (-)-salinosporamide A

A concise and stereoselective total synthesis of (-)-salinosporamide A (1), a potent inhibitor of the 20S proteasome that is in clinical development as an anticancer drug candidate, has been accomplished in 14 steps with 19% overall yield from 4-pentenoic acid. Our synthesis features a stereoselective alkylation utilizing a chiral auxiliary, formation of a pyrrolidine unit, and oxidation of the pyrrolidine to a γ-lactam. To demonstrate the scalability of our synthesis, (-)-salinosporamide A has been synthesized on a gram scale.

An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy

A general and efficient synthesis of carbocyclic and hexenopyranosyl nucleosides has been developed. The strategy combines three key transformations: an asymmetric aldol addition to establish the relative and absolute configuration of the pseudosugar, a ring-closing metathesis to construct the pseudosugar ring, and a Trost-type palladium(0)-mediated substitution to assemble the pseudosugar and the aromatic base. Carbovir, abacavir, and their 2'-methyl derivatives as well as hexenopyranosyl nucleoside analogues have been prepared by this sequence.