Chiral synthesis of 5-hydroxy-(L)-pipecolic acids from (L)-glutamic acid
✍ Scribed by Patrick D Bailey; Justin S Bryans
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 204 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A stereo-and enantio-specific synthesis of the natural1 occurring cis-%hydroxy-(L)-pipecolic acid (3) is described, starting from Z-(L -glutamic the key step involves c chsation of a Y, to trans-%hydroxy-(L -pipecolic acl 3 3 rotected chlorohydrin, and also gives access acid, .
📜 SIMILAR VOLUMES
## Abstract Enantiopure (3__S__,4__R__)‐ and (3__S__,4__S__)‐3‐amino‐4‐hydroxyhexanoic acids and (4__S__,5__R__)‐ and (4__S__,5__S__)‐4‐amino‐5‐hydroxyheptanoic acid derivatives have been prepared by stereodivergent synthesis from L‐aspartic and L‐glutamic acids, respectively. The stereochemistry a
L-Glutamic acid has been converted into a separable mixture of D-amicetonoand L-rhodinono-y-lactones by a sequence involving transformation into (S)-y-carboxy-y-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohyd