Bulletin of the Korean Chemical Society

  • 제22권6호
  • /
  • Pages.553-558
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  • 2001
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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A Stereoselective Synthesis of 1 $\beta$-Aminocarbapenems.

  • 발행 : 20010600
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초록

A stereoselective synthesis of $1\beta-aminocarbapenems$ (11a-c) starting from-4-acetoxy-2-axetidinone derivative 4 is described. 4-Acetoxy-2-azetidinone derivative (4) was reacted with lithium enolate of benzophenone limine of glycine phenyl ester (5f) to give alkylated product (R)-6f in good yield with high diastereoselectivity. The alkylated procudt (R)-6f was transformed to thioesters (7a-c) by transesterification with thiols, Thioesters (7a-c) were converted to their oxalimides (8a-c), followed by the phosphite-mediated reductive cyclization to give carbapenems (9a-c). Removal of all protecting groups of carbapenems (9a-c) afforded $1\beta-aminocarbapenems$ (11a-c).

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참고문헌

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