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Synthesis of (2R,4R)- and (2S,4S)-4-hydroxypipecolic acid derivatives and (2S,4S)-(−)-SS20846A

✍ Scribed by Mark Sabat; Carl R Johnson

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
104 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio-and stereochemistry of key intermediates.

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