【文章名】Synthesis of 2,3- and 3,4-methanoamino acid equivalents with stereochemical diversity and their conversion into the tripeptide proteasome inhibitor belactosin A and its highly potent cis-cyclopropane stereoisomer.
Synthesis of 2,3- and 3,4-methanoamino acid equivalents with stereochemical diversity and their conversion into the tripeptide proteasome inhibitor belactosin A and its highly potent cis-cyclopropane stereoisomer.
[摘要]：A series of chiral 2,3- and 3,4-methanoamino acid equiv. of stereochem. diversity were designed and synthesized from our chiral cyclopropane units, using a diastereoselective Grignard addn. with (R)- or (S)-t-butanesulfinyl imines as the key step. These equiv. were converted into the proteasome inhibitor belactosin A and its cis-cyclopropane stereoisomer. The unnatural cis-isomer was shown to be more than twice as potent as belactosin A as a proteasome inhibitor.
