- Asymmetric Synthesis of (1'R,3R,4R)-4-Acetoxy-3(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone and Other 3-(1'-Hydroxyethyl)-2-azetidinones from (S)-(+)-Ethyl 3-Hydroxybutanoate: Formal Total Synthesis of (+)-Thienamycin
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The synthesis of (1'R,3R,4R)-4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone, an important precursor for synthesis of carbapenems and penems, is detailed.The methodology utilized relies on the addition, cyclization reaction between the dianion of (S)-(+)-ethyl 3-hydroxybutanoate and N-arylaldimines.The syntheses of other useful optically active 3-(hydroxyethyl)-2-azetidinones are presented.A study of factors influencing the stereochemistry in the addition, cyclization reaction for the formation of 3-(1'-hydroxyethyl)-2-azetidinones is detailed.
- Georg, Gunda I.,Kant, Joydeep,Gill, Harpal S.
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p. 1129 - 1135
(2007/10/02)
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- Stereo- and Enantio-controlled Synthesis of Chiral Intermediates for the Total Synthesis of Thienamycin and Related β-Lactam Antibiotics from 3-Hydroxybutyrates
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The synthesis of (1'R,3S,4S)- and (1'R,3S,4R)-3-(1'-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone from ethyl (S)-3-hydroxybutyrate is reported.
- Georg, Gunda I.,Gill, Harpal S.
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p. 1433 - 1435
(2007/10/02)
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