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Synlett 1995; 1995(9): 915-917
DOI: 10.1055/s-1995-5144
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Asymmetric Radical Cyclization Induced by a Matched Pair of Chiral Auxiliaries: Synthesis of a Chiral 1β-Methylcarbapenem Key Intermediate

Hiroyuki Ishibashi* , Chisato Kameoka, Kazuya Kodama, Masazumi Ikeda1
  • *Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan
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Publication Date:
31 December 2000 (online)

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The chiral 1β-methylcarbapenem key intermediate 1 was synthesized using an asymmetric radical cyclization of N-vinylic α-bromo amide 16 bearing a matched pair of chiral auxiliaries as a key step.

asymmetric induction - 1β-methylcarbapenem - Mitsunobu reaction - radical cyclization - ruthenium tetroxide oxidation

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