Jasmine lactone, preparation

Jasmine lactone, preparation, 787 Jet fuel, autoxidation, 665 Jojoba oil, ozonized, 718 Juice, hydrogen peroxide content, 653... 

Figure 3.63 Preparation of jasmine lactone with bis( trimethylsilyl)peroxide.

The aldol reaction in the presence of an acyclic amino acid has been harnessed in total synthesis. Takabe reported the organocatalytic ot-hydro)ymethylation of a cyclic ketone in aqueous formaldehyde with L-threonine, as the key step for the formal synthesis of chiral jasmine lactone. In a similar way, the team of Chen and Chai prepared several cyclohexanone derivatives. Much more recently, a synthesis of phaitanthrin A by aldol reaction of tryptanthrin with acetone in the presence of the potassium salt of L-phenylalanine has been performed in gram-scale quantities. Numerous derivatives have been obtained with yields of up to 98% and ee of up to 99%. 

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