A second-generation synthesis of polypyrrolinone nonpeptidomimetics: prelude to the synthesis of polypyrrolinones on solid support.
[reaction: see text] A second-generation asymmetric synthesis of polypyrrolinones (3) has been achieved exploiting scalemic alpha-aminolactones (1) as building blocks. Imine formation between an appropriate lactone (1) and aldehyde (2), followed in turn by pyrrolinone ring construction promoted by KHMDS in the presence of 18-crown-6 and modified Swern oxidation furnished pyrrolinone aldehyde 3. This iterative, efficient three-step protocol paves the way for the synthesis of polypyrrolinones on solid support.
Smith
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Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Liu
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H
Hirschmann
R
R
D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors*; D004121:Dimethyl Sulfoxide; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000201:enzymology*; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry
D017320:HIV Protease Inhibitors; D011760:Pyrrolidinones; D016282:Aspartic Acid Endopeptidases; D004121:Dimethyl Sulfoxide