70981-24-7Relevant academic research and scientific papers
Enantioselective synthesis of both the enantiomers of jasmine ketolactone and its epimer
Inoue, Munenori,Nishi, Tsunehiro,Kitahara, Takeshi
, p. 1122 - 1124 (1999)
The enantioselective synthesis of jasmine ketolactone 1, which was isolated as a component of Italian jasmine oil, and its epimer 2 is described. Lactones 1 and 2 were synthesized in 5 and 4 steps, respectively, by Yamaguchi's macrolactonization method fr
Cationic ruthenium allenylidene complexes as catalysts for ring closing olefin metathesis
Fuerstner, Alois,Liebl, Monika,Lehmann, Christian W.,Picquet, Michel,Kunz, Rainer,Bruneau, Christian,Touchard, Daniel,Dixneuf, Pierre H.
, p. 1847 - 1857 (2007/10/03)
A series of well accessible cationic ruthenium allenylidene complexes of the general type [(η6-arene)(R3P)RuCl(=C=C=CR′2)] + X- is described which constitute a new class of pre-catalysts for ring closing olefin metathesis reactions (RCM) and provide an unprecedented example for the involvement of metal allenylidenes in catalysis. They effect the cyclization of various functionalized dienes and enynes with good to excellent yields and show a great tolerance towards an array of functional groups. Systematic variations of their basic structural motif have provided insights into the essential parameters responsible for catalytic activity which can be enhanced further by addition of Lewis or Bronsted acids, by irradiation with UV light, or by the adequate choice of the "non-coordinating" counterion X-. The latter turned out to play a particularly important role in determining the rate and selectivity of the reaction. A similarly pronounced influence is exerted by remote substituents on the allenylidene residue which indicates that this ligand (or a ligand derived thereof) may remain attached to the metal throughout the catalytic process. X-ray crystal structures of the catalytically active allenylidene complexes 3b · PF6 and 15 · OTf as well as of the chelate complex 10 required for the preparation of the latter catalyst are reported.
Metathesis-based synthesis of jasmonate and homojasmonate lactones, candidates for extracellular quorum sensing molecules in Candida albicans
Cho, Su C.,Dussault, Patrick H.,Lisec, Amber D.,Jensen, Ellen C.,Nickerson, Kenneth W.
, p. 193 - 196 (2007/10/03)
Ring-closing metathesis of jasmonate esters is shown to provide a rapid entry to jasmonate lactones. The lactones were investigated as possible quorum sensing molecules for the fungi Candida albicans. Assays demonstrated no effect on fungal morphology at concentrations up to 96 μM.
The First Synthesis of a 10-Membered Ring by Olefin Metathesis: Jasmine Ketolactone
Fürstner, Alois,Müller, Thomas
, p. 1010 - 1012 (2007/10/03)
An unprecedentedly short route to jasmine ketolactone (Z)-2 and its E-isomer is described, which is based on the efficient formation of the 10-membered ring via ring closing olefin metathesis (RCM) of diene 8. The latter is conveniently prepared by a three component coupling reaction consisting of the 1,4-addition of the lithium enolate of 3-butenyl (diphenylmethylsilyl)acetate 6 to 2-cyclopentenone and subsequent trapping of the enolate thus formed with allyl iodide.
SYNTHESIS OF (+/-)-JASMINE KETOLACTONE BY TRANSANNULAR MICHAEL REACTION
Shimizu, Isao,Nakagawa, Hiroya
, p. 4957 - 4958 (2007/10/02)
Transannular Michael reaction of (2E,9Z)-6-oxo-2,9-dodecadienolide gave (+/-)-Jasmine Ketolactone in 69 percent yield.
Synthesis of Jasmine Ketolactone
Kitahara,Takeshi,Iwamoto, Minoru,Takagi, Yoshikazu,Mori, Kenji,Matsui, Masanao
, p. 1731 - 1734 (2007/10/02)
The synthesis of jasmine ketolactone 3, a minor component of Italian jasmine oil, via the intramolecular Michael reaction is described.
