Trans-4-hydroxypipecolic acid

Dihydroxylation of olefins followed by oxidation with periodate leads to cyclization and the corresponding carbinolamine. This can then be reduced to the piperidine <2005JOC10182> (Scheme 12). The strategy was used in the synthesis of both the (2A,3i )-3-hydroxypipecolic acid 13 and (2 5, 3A)-3-hydroxypipecolic acid 14 from D-serine. Variations in this strategy toward both trans-isomers of the 3-hydroxypipecolic acid moiety are shown in Schemes 13 and 14. The initial stereochemistry was introduced using Sharpless method <2005JOC360>. 

Ring openings interrelate cis-3- and cw-4-methylated pro-line (30, 31) as well as pipecolic acid (17) into these metabolic pathways. Addition of water to baikiain (28) can lead to trans-4- and/or rm j-5-hydroxypipecolic acid (32, 33). 4-Methylglutamic acid (9) can feed into cij-4-methylproline (31), 4-methyleneglutamic acid (26) into 4-methylenepro-... 

DL- and DL-al/o-5-hydroxy[6- C]lysine is transformed into cis- and trans-5-hydroxypipecolic acid and into N -acetyl-5-hydroxylysine in Gleditsia tri-acanthos ° 5-Hydroxypipecolic acid is not further metabolized and 90% of the radioactivity was retained in 5-hydroxypipecolic acid, indicating that all four diastereomers of the added hydroxylysine were utilized. 

Ferreira, R, Greek, C. and Genet, J.P. (1997) Stereocontrolled syntheses of trans-3-hydroxypipecolic acids and application to (-)-Swainsonine. Bull. Soc. Chim. Fr., 134, 615-621. 

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