Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid

DOI: 10.1248/cpb.45.255

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 255 - 259 (1997)

Update date:2022-08-03

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Authors:

Arakawa, Yasushi

Yasuda, Mika

Ohnishi, Masafumi

Yoshifuji, Shigeyuki

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Article abstract of DOI:10.1248/cpb.45.255

Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.

Full text of DOI:10.1248/cpb.45.255

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