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Progress toward the synthesis of piperazimycin A: exploration of the synthesis of γ-hydroxy and γ-chloropiperazic acids

✍ Scribed by J. Phillip Kennedy; John T. Brogan; Craig W. Lindsley

Book ID
104095375
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
257 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

expedient route to key (3S,5S)-and (3R,5R)-c-hydroxy and (3R,5S)-c-chloropiperazic acids, was developed en route to a total synthesis of piperazimycin A.

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Efficient Synthesis of γ-Oxo-and γ-Hydroxy-α-amino Acids. -Reduction of aminoester (Va) with Zn(BH 4 ) 2 permits intermediate isolation of the γ-hydroxy derivative, which is converted to lactone (IX) during silica gel chromatography. -(MERLA, B.;