18309-32-5Relevant articles and documents
Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri
Passaro, Linda C.,Webster, Francis X.
, p. 2896 - 2899 (2004)
The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3-NalO4, and methylenation with Zn/CH 2Br2/TiCl4.
Optical Control of Cannabinoid Receptor 2-Mediated Ca2+Release Enabled by Synthesis of Photoswitchable Probes
Sarott, Roman C.,Viray, Alexander E. G.,Pfaff, Patrick,Sadybekov, Anastasiia,Rajic, Gabriela,Katritch, Vsevolod,Carreira, Erick M.,Frank, James A.
, p. 736 - 743 (2021)
Cannabinoid receptor 2 (CB2) is a promising target for the treatment of neuroinflammation and other diseases. However, a lack of understanding of its complex signaling in cells and tissues complicates the therapeutic exploitation of CB2 as a drug target. We show for the first time that benchmark CB2 agonist HU308 increases cytosolic Ca2+ levels in AtT-20(CB2) cells via CB2 and phospholipase C. The synthesis of photoswitchable derivatives of HU308 from the common building block 3-OTf-HU308 enables optical control over this pathway with spatiotemporal precision, as demonstrated in a real-time Ca2+ fluorescence assay. Our findings reveal a novel messenger pathway by which HU308 and its derivatives affect cellular excitability, and they demonstrate the utility of chemical photoswitches to control and monitor CB2 signaling in real-time
Individual stereoisomers of verbenol and verbenone express bioactive features
Ivanov, Marija,Kovalenko, Vitaly,Svirid, Anastasia,Kosti?, Marina,Petrovi?, Jovana,Stojkovi?, Dejan
, (2021/12/13)
Naturally occurring terpene core compounds have been used extensively in both pharmaceutical and cosmetic industry. However, since chirality of these compounds has profound influence on the level of their bioactivity, the aim of the present study was to a
Stereospecific synthesis of S-(?)-trans-verbenol and its antipode by inversion of sterically hindered alcohols
Fang, Jia-Xing,Kong, Xiang-Bo,Liu, Fu,Zhang, Su-Fang,Zhang, Zhen
, (2020/12/15)
S-(?)-trans-Verbenol (1) and its antipode, R-(+)-trans-verbenol (1′) have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols (1 and 1′) from commercially available starting materials S-α-pinene and R-α-pinene was reported. The key steps were mainly depended on the effective SN2 stereo-inversion of the hydroxy group of sterically hindered alcohols (3 and 3′), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.
Highly Selective, Amine-Derived Cannabinoid Receptor 2 Probes
Carreira, Erick M.,Grether, Uwe,Guba, Wolfgang,Osterwald, Anja,Sarott, Roman C.,Ullmer, Christoph,Westphal, Matthias V.,Zirwes, Elisabeth A.
supporting information, p. 1380 - 1387 (2020/02/05)
The endocannabinoid (eCB) system is implied in various human diseases ranging from central nervous system to autoimmune disorders. Cannabinoid receptor 2 (CB2R) is an integral component of the eCB system. Yet, the downstream effects elicited by this G protein-coupled receptor upon binding of endogenous or synthetic ligands are insufficiently understood—likely due to the limited arsenal of reliable biological and chemical tools. Herein, we report the design and synthesis of CB2R-selective cannabinoids along with their in vitro pharmacological characterization (binding and functional studies). They combine structural features of HU-308 and AM841 to give chimeric ligands that emerge as potent CB2R agonists with high selectivity over the closely related cannabinoid receptor 1 (CB1R). The synthesis work includes convenient preparation of substituted resorcinols often found in cannabinoids. The utility of the synthetic cannabinoids in this study is showcased by preparation of the most selective high-affinity fluorescent probe for CB2R to date.
Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene
Kmieciak, Anna,Krzemiński, Marek P.
supporting information, p. 2493 - 2499 (2019/12/11)
New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1R,2R,4S,5R)-3-methyleneneoisoverbanol and (1R,2R,3R,5R)-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration–oxidation reaction proceeding from the less hindered site providing a trans relationship between the hydroxy and the phosphine substituents.
Cis-dioxo-Mo(VI) salophen complex supported on Fe3O4@SiO2 nanoparticles as an efficient magnetically separable and reusable nanocatalyst for selective epoxidation of olefins
Bezaatpour, Abolfazl,Khatami, Sahar,Nejati, Kamellia
, p. 2105 - 2115 (2017/09/13)
In this work, paramagnetic Fe3O4/SiO2 nanoparticles were synthesized, characterized and functionalized with dioxo-Mo(VI) tetradentate Schiff base complex and characterized using IR spectroscopy, X-ray powder diffraction spectroscopy, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, diffuse reflectance spectroscopy and atomic absorption spectroscopy. Catalyst was used for the selective epoxidation of cyclooctene, cyclohexene, styrene, indene, α-pinene, 1-hepten, 1-octene, 1-dodecen and trans-stilbene using tert-butyl hydroperoxide as oxidant in 1,2-dichloroethane. This catalyst is efficient for oxidation of cyclooctene with a 100% selectivity for epoxidation with 100% conversion in 1?h. After the reaction, the magnetic nanocatalyst was easily separated by simply applying an external magnetic field and was used at least five successive times without significant decrease in conversion.[Figure not available: see fulltext.].
Potent Odorants of Characteristic Floral/Sweet Odor in Chinese Chrysanthemum Flower Tea Infusion
Kaneko, Shu,Chen, Jingxiu,Wu, Jieming,Suzuki, Yuto,Ma, Lin,Kumazawa, Kenji
, p. 10058 - 10063 (2017/11/30)
An investigation using the aroma extract dilution analysis (AEDA) technique applied to the aroma concentrates prepared from the tea infusions of two different types of Chinese chrysanthemum flowers (flower buds, blooming flowers) revealed that 29 aroma peaks were detected in the aroma concentrates, and 17 compounds were newly identified or tentatively identified in the chrysanthemum flower tea. AEDA also revealed that the aroma peaks having high flavor dilution factors mainly consisted of a floral/sweet note in addition to metallic and phenol-like/spicy notes. Among them, four aroma peaks having a floral/sweet were identified as verbenone, ethyl 3-phenylpropanoate, propyl 3-phenylpropanoate, and ethyl cinnamate, and a semiquantitative analysis revealed that the flower buds were rich in these compounds. Furthermore, a chiral analysis revealed that (-)-verbenone existed in both flowers at a 3 times higher concentration than (+)-verbenone. Additionally, because the detection threshold of (-)-verbenone was lower than that of the (+)-verbenone, it is concluded that the (-)-isomer was a main contributor of the aroma peak of verbenone in the chrysanthemum flower tea.
Crystallization of bisulfite derivatives of enantiomerically enriched verbenone
Kovalenko,Prat’ko,Prokhorevich
, p. 1598 - 1600 (2017/12/08)
After separation of crystalline bisulfite derivatives of enantiomerically enriched (1S)- and (1R)-verbenones, steam distillation of the filtrates afforded (1S)- and (1R)-verbenones whose optical purity was higher by 30 and 20%, respectively, than that of
Synthesis of new enantiomerically pure β-amino alcohols of the pinane series
Frolova,Sudarikov,Alekseev,Banina,Slepukhin,Kutchin
, p. 335 - 343 (2017/05/09)
A series of new β-amino alcohols with pinane structure, (+)- and (?)-3α-amino-10β-pinan-4β-ols, 4β-amino-10β-pinan-3α-ol, and 4α-amino-10β-pinan-3α-ol have been synthesized with the goal of using them as organocatalysts in the aldol reaction of isatin with acetone.
