154774-34-2

Upstream product

• 69143-05-1 (E)-4-methyl-pent-2-en-1-ol 
• 481055-09-8 7a-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one 
• 78-84-2 isobutyraldehyde 
• 154774-33-1 (S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-3-phenyl-1H-pyrrolo[1,2-c]oxazole 
• 154774-32-0 (3S,7aR)-6-Methyl-3-phenyl-1,7a-dihydro-pyrrolo[1,2-c]oxazol-5-one 
• 118918-76-6 (2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one 
• 481055-07-6 5-(tert-butyl-dimethyl-silanyloxymethyl)-5-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-methyl-1,5-dihydro-pyrrol-2-one 
• 481055-05-4 2-(tert-butyl-dimethyl-silanyloxymethyl)-2-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4-methyl-2,5-dihydro-1H-pyrrole 
• 481055-06-5 2-(tert-butyl-dimethyl-silanyloxymethyl)-2-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4-methyl-2H-pyrrole 
• 1015841-27-6 (2R,3S)-1,3-bis(tert-butyldimethylsilanyloxy)-4-methyl-pentan-2-amine 
• 481055-08-7 (R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-5-hydroxymethyl-3-methyl-1,5-dihydro-pyrrol-2-one 
• 481055-02-1 4-[1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-trichloro-methyl-4,5-dihydro-oxazole 
• 481055-03-2 (2R,3S)-2-amino-3-(tert-butyldimethylsilanyloxy)-4-methyl-pentan-1-ol 
• 125414-30-4 (1'S,4R)-4-(2'-methyl-1'-hydroxypropyl)-2-(trichloromethyl)-2-oxazoline 

Downstream Products

• 154774-44-4 Acetic acid (S)-2-methyl-1-((3aR,3bR,6S,8aR)-8a-methyl-8-oxo-6-phenyl-2-thioxo-dihydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-3b-yl)-propyl ester 
• 154774-36-4 Acetic acid (S)-1-((3S,6R,7R,7aS)-6,7-dihydroxy-6-methyl-5-oxo-3-phenyl-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-2-methyl-propyl ester 
• 133343-34-7 Lactacystin 
• 145451-97-4 (3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid 
• 154774-35-3 Acetic acid (S)-2-methyl-1-((3S,7aR)-6-methyl-5-oxo-3-phenyl-5H-pyrrolo[1,2-c]oxazol-7a-yl)-propyl ester 

Relevant academic research and scientific papers

An enantioselective formal synthesis of the proteasome inhibitor (+)-lactacystin

An enantioselective formal synthesis of the proteasome inhibitor (+)-lactacystin has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The key cyclisation precursor was synthesised in high diastereomeric excess using a combination of known procedures, with the two key asymmetric centres being introduced via a Sharpless asymmetric epoxidation reaction. KHMDS induced 1,5-CH insertion produced a 3-pyrroline product, which was oxidised to the corresponding 3-pyrrolin-2-one using (1) TPAP/NMO; (2) NaClO2; (3) NaBH4. The formal synthesis was then completed with a few standard functional group interconversions.