Jasmine lactone

Jacobson-Hugershofi synthesis benzothiazoles, 5, 135 Japp-KJingemann reaction JV-arylhydrazones from, 4, 337 1,2,4-triazole synthesis by, 5, 768 Jasmine lactone synthesis, 3, 847 Jasminine occurrence, 2, 626 y-Jasmolactone synthesis, 4, 674 cis-Jasmone synthesis, 1, 422, 427 Jatropham synthesis, 1, 426 Josephson junctions, 1, 359 Juliprospine... 

Jasmine lactone 20 is synthesized from 2-[(Z)-2-pentenyl]cyclopentanone 19 in several steps (equation 33) ° without any protection of the carbon-carbon double bond. The hytoxy acid 21 was formed as a side product. 

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

Jasmin lactone -m osmanthus flowers [OILS, ESSENTIAL] (Vol 17)... 

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

Photo-oxidation of olefins in pyridine solution in the presence of FeCIs has been found to take one of three courses, depending on the substitution pattern of the substrate olefin. These routes lead to formation of a-chloroketones, gem-dichloroketones, and a,-dichloroketones, and have all been illustrated by their use in actual syntheses. a-Chloroketones have also been produced by irradiation of pyridine solutions of vinylsUanes or vinyl sulphides under similar conditions. DCA-sensitized photo-oxidation of l,2-diphenyl-3,3,4,4-tetramethylcyclobutene in MeCN leads to the corresponding ozonide in a process which occurs by initial formation of an oxirane. Jasmine lactone (12 ... 

This sequence has been used for the synthesis of jasmine lactone (7) as formulated. 

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%. 

In addition to the 5-lactones of structure (41), other lactonic aroma components with a saturated ring are known, the structure of which, however, is somewhat different from that of the n-series represented by (41). These are 6-hydroxy-5-hexanolide (42), identified in tomato (557), and three cyclic compounds carrying an unsaturated chain in position 5, viz. (Z)-7-decen-5-olide (jasmine lactone) (44) 712), identified in the flavor of black tea (50) together with methyl jasmonate (779). (Z)-9-dodecen-5-olide (45) and (Z)-9-tetradecen-5-olide (46), the latter two lactones having been isolated from butter flavor (50, 725). On the other hand, lactone (43) was isolated from milk where it is present in a quantity of 10 pg/kg (0.001 ppb) (247) this quantity, however, is probably much lower than the threshold value. 

Yamanishi, T., M. Kawatsu, T. Yokoyama, and Y. Nakatani Methyl Jasmonate and Lactones Including Jasmine Lactone in Ceylon Tea. Agric. Bull. Chem. 37, 1075 (1973). 

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