Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid
โ Scribed by Clinton A Brooks; Daniel L Comins
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 84 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
An asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid was accomplished in eight steps and 31% overall yield.
๐ SIMILAR VOLUMES
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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
A synthetic route to (2S,3S)-3-hydroxypipecolic acid was achieved from readily available nonchiral pool starting material cis-2-butene-1,4-diol and involved Claisen orthoester rearrangement, Sharpless asymmetric dihydroxylation and intramolecular lactamisation of azido lactone as the key steps.