50373-53-0Relevant articles and documents
Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol
Takada, Yuki,Caner, Joaquim,Kaliyamoorthy, Selvam,Naka, Hiroshi,Saito, Susumu
supporting information, p. 18025 - 18032 (2017/12/08)
We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.
METHOD OF MONITORING AND/OR CONTROLLING THYSANOPTERA
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Page/Page column 35-36, (2014/05/24)
The present invention provides a method of monitoring or controlling Thysanoptera (hereafter thrips) using a behaviour-modifying compound of Formula (1), wherein Formula (1) is: where R1 is a C2-C8 straight or branched alkenyl group and the * denotes a stereocentre. Suitably, the method involves providing the behaviour-modifying compound at a pre- determined location. Typically the behaviour-modifying compound is released or broadcast within an area infested (or potentially infested) by thrips. This can be achieved by using a lure or other release device comprising a compound of Formula (1), for example to attract the thrips to a trap.
Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone
Pepper, Henry P.,Tulip, Stephen J.,Nakano, Yuji,George, Jonathan H.
, p. 2564 - 2573 (2014/04/17)
A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.
Chemomicrobial synthesis of (R)- and (S)-lavandulol
Gliszczynska, Anna,Bonikowski, Radoslaw,Kula, Jozef,Wawrzenczyk, Czeslaw,Ciolak, Kornelia
, p. 4461 - 4463 (2011/09/19)
(R)- and (S)-Lavandulol are important compounds in the cosmetics industry and in pheromone research. We have developed syntheses of (R)- and (S)-lavandulol from (S)- and (R)-limonene, respectively, by microbial Baeyer-Villiger oxidation of the intermediate unsaturated hydroxy ketone. It has been found that the same strain of Acremonium roseum can be successfully used in the key step of the synthesis of both enantiomers of lavandulol.
Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol
Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho
, p. 2682 - 2685 (2011/06/26)
Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: Simple preparation of enantiomerically pure (R)-lavandulol
Zada, Anat,Dunkelblum, Ezra
, p. 230 - 233 (2007/10/03)
(R)- and (S)-lavandulol and their esters are important compounds in perfumery and have recently become significant in pheromone research. (R)-Lavandulol and its esters, as well as the esters of (S)-lavandulol have been identified as sex and aggregation pheromones in two mealybugs, in thrips and in weevils. We report a convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride. This method does not require tedious chromatographic separation and is particularly suitable for the preparation of enantiomerically pure (R)-lavandulol with 98% ee in one resolution cycle. The (S)-lavandulol with 90% ee can be obtained by a second resolution cycle.
Enzymatic transesterification of racemic lavandulol: Preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate
Zada, Anat,Harel, Miriam
, p. 2339 - 2343 (2007/10/03)
(R) and (S)-lavandulol are important compounds in the cosmetics industry and in pheromone research. The senecioyl ester of (S)-lavandulyl has recently been identified as the sex pheromone of the vine mealybug, a significant pest in vineyards. We herein report the preparation of the two enantiomers of lavandulol and lavandulyl senecioate, starting from racemic lavandulol. The preparation is based on a two-cycle enzymatic transesterification of racemic lavandulol with vinyl acetate using Porcine pancreas lipase. High enantioselectivity was achieved while the preparation yielded (R)-lavandulol with 96.7% ee and (S)-lavandulol with 92.6% ee.
General Chiral Route to Irregular Monoterpenes via a Common Intermediate: Syntheses of (S)-Lavandulol, cis-(1S,3R)-Chrysanthemol, (1S,2R)-Rothrockene, and (R)-Santolinatriene
Takano, Seiichi,Tanaka, Mariko,Seo, Kenji,Hirama, Michiyasu,Ogasawara, Kunio
, p. 931 - 936 (2007/10/02)
Treatment of (S)-O-benzylglycidol (6) with senecioic acid in the presence of LDA, followed by acid workup, yielded a mixture of lactones 9 and 10, whose enolate 11 on exposure to hydrochloric acid (10percent) gave the α/γ-syn lactone 12 as a single produc
C45- and C50-Carotenoids, 1st Communication. Synthesis of (R)- and (S)-Lavandulol
Kramer, Andreas,Pfander, Hanspeter
, p. 293 - 301 (2007/10/02)
Starting with methyl (3R)-3-hydroxybutanoate ((R)-7) and ethyl (3S)-3-hydroxybutanoate ((S)-11), respectively, (R)- and (S)-lavandulol ((R)-1 and (S)-1) were synthesized with high optical purity.The synthesized key intermediates (R)-6 and (S)-6 are suitable compounds for the synthesis of optically active acyclic C45- and C50-carotenoids.
