292615-59-9

Upstream product

• 4316-35-2 acetophenone dimethyl acetal 
• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 292615-60-2 (+)-(2R,5S,7S)-2-methyl-2-phenyl-7-(phenylmethyl)-1-aza-3-oxabicyclo[3.3.0]octan-8-one 
• 637019-57-9 (2R,5S,7S,1'R)-7-(N-tosylaminofuran-2-yl-methyl)-8-oxo-2-phenyl-2-methyl-1-aza-3-oxabicyclo[3.3.0]octane 
• 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 
• 154226-60-5 omuralide 
• 637019-59-1 (2R,5S,7R,1'S)-7-(N-tosylaminofuran-2-ylmethyl)-8-oxo-2-phenyl-2-methyl-1-aza-3-oxabicyclo[3.3.0]octane 

Relevant academic research and scientific papers

On the diastereoselectivity of alkylations of bicyclic lactams

The diastereoselectivity in the alkylation of the enolates of bicyclic lactams 2 derived from pyroglutaminol la has been found to depend upon the nature of the hemiaminal ether protecting group. Although exo-alkylation has been widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is postulated that this is a result of the opening of the bicyclic structure of the enolate derived from 2d, and the consequent stereoelectronic facilitation of endo-facial attack.

Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin

(Figure Presented). Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation chemo- and stereoselectively constructed the tetra- and trisubstituted carbon centers, respectively. The obtained bicycle was transformed into the target compound in a concise manner. The present total synthesis demonstrates the power of the direct C(sp3)-H functionalizations for the assembly of multiple functionalized structures of natural products.