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Stereoselective Total Synthesis of cis - and trans -3-Hydroxypipecolic Acid

✍ Scribed by Liang, Ningning; Datta, Apurba


Book ID
127194068
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
112 KB
Volume
70
Category
Article
ISSN
0022-3263

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A Stereoselective Total Synthesis of cis
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An alternative stereoselective synthesis
✍ Mansour Haddad; Marc LarchevΓͺque πŸ“‚ Article πŸ“… 2001 πŸ› Elsevier Science 🌐 French βš– 71 KB

The enantioselective synthesis of trans-(2R,3R)-3-hydroxypipecolic acid 1b is presented, starting from O-protected methyl mandelate as chiral source. The synthesis involved a regioselective intramolecular nucleophilic substitution of an azido epoxide as the key step .

Asymmetric total synthesis of (2S,3S)-3-
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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.