Asymmetric Synthesis of Both the Enantiomers of trans-3-Hydroxypipecolic Acid

Abstract

Both the enantiomers of trans-3-hydroxypipecolic acid have been synthesized employing the Sharpless asymmetric dihydroxylation and epoxidation as the key steps starting from a commercially available starting material 1,4-butanediol.

In the Arena of Enantioselective Synthesis, Titanium Complexes Wear the Laurel Wreath

“…Oxido-functionalized longer chain allylic alcohols, such as compound 1m , can be epoxidized under substoichiometric standard conditions, to give in this case the expected epoxide 5m with a moderate yield but with an excellent enantioselectivity (Scheme ). This epoxide has been used in the synthesis of (−)-swainsonine ( 31 ) 61 and transformed into trans -3-hydroxypipecolic acid ( 32 ) . The former is a potent inhibitor of α- d -mannosidase and mannosidase II, as well as an anticancer agent.…”

A Shimizu Non‐Aldol Approach to the Formal Total Synthesis of Palmerolide A

“…The combined organic extracts were washed with brine, dried over Na 2 SO 4 , and concentrated under reduced pressure. Purification by column chromatography (30–40 % ethyl acetate/hexanes) afforded the alcohol (4.72 g, 92 %) as a viscous oil 24a . R f =0.40 (30 % ethyl acetate/hexanes); IR (neat): $\tilde \nu $ =3423, 1687, 1612, 1513, 1463, 1302, 1248, 1174, 1093, 1034, 970 cm −1 ; 1 H NMR (CDCl 3 , 400 MHz ): δ =7.26 (d, J =8.8 Hz, 2 H), 6.88 (d, J =8.6 Hz, 2 H), 5.71–5.59 (m, 2 H), 4.43 (s, 2 H), 4.07 (d, J =4.6 Hz, 2 H), 3.80 (s, 3 H), 3.45 (t, J =6.4 Hz, 2 H), 2.16–2.10 (m, 2 H), 1.76 (s, 1 H), 1.72–1.65 ppm (m, 2 H); 13 C NMR (100 MHz , CDCl 3 ): δ =159.0, 132.3, 130.5, 129.3, 129.2, 113.6, 72.4, 69.2, 63.5, 55.2, 29.0, 28.7 ppm.…”

The 3‐Hydroxypiperidine Skeleton: Key Element in Natural Product Synthesis

“…In a few steps, intermediate 40 was further converted into the natural product 2 . Several years later, Kumar and co‐workers published a total synthesis of both trans ‐3‐hydroxypipecolic acids by a similar strategy 33…”