Monatin, synthesis

Synthesis of (—)-monatin (524), a high-intensity sweetening agent, was achieved by chelation-controlled cycloaddition of chiral oxazinone-derived nitrone (16 ) to allyl alcohol (520) in the presence of MgBr2 OEt2 (Scheme 2.248) (746). 

Monatin, 4-hydroxy-4-(indoT3-ylmethyl) glutamic acid, a high-intensity sweet, natural compound. Monatin was isolated from the roots of Schlerochiton ilicifolius, a spinyleaved hardwood shrub growing in South Africa. The synthesis of the four... 

Enzymatic synthesis of a precursor of monatin (36) using pyruvate-dependent aidoiases from Pseudomonas taetrolens (PyAp... 

To demonstrate the synthetic utility of the cycloaddition of nitrone (S)-29 with alkene 78, synthesis of the (25,4/ )-monatin (80) from cycloadduct 79e was examined (Scheme 6.22). Thus, hydrogenolysis of 79e by using Perlman s catalyst gave a lactone, which, on treatment with LiOH in MeOH-H20 at room temperature, underwent hydrolysis to give 80 without isomerization in 33% yield. 

---