13362-52-2Relevant articles and documents
Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)
Lu, Zhengchang,Liu, Wei,Pan, Hongyu,Zhang, Dawei
, (2018)
A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 μg, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 μg. Compared with the existing routes, this synthetic approach is operationally simple, good-yielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.
The first examples of a Meta-benzannulation from the reaction of Fischer carbene complexes with alkynes
Wang, Huan,Huang, Jie,Wulff, William D.,Rheingold, Arnold L.
, p. 8980 - 8981 (2003)
The intramolecular benzannulations of carbene complexes with alkynes are examined where the alkyne is tethered to the α-carbon of the vinyl carbene complex. These reactions are sensitive to the length of the tether and to the nature of the solvent. With a tether length of 16 methylenes, the reaction occurs in the same fashion as the intermolecular reactions to give a p-cyclophane. With intermediate tether lengths (n = 10, 13), the reaction gives an additional p-cyclophane in which the two oxygen substituents are meta on the arene ring. This type of product is unprecedented from the reaction of carbene complexes and alkynes and is quite surprising because the formation of this product requires that the carbon-carbon bond between the α- and β-carbons of the vinyl carbene complex is broken. A mechanism is proposed to account for this process which involves the crossed intramolecular [2 + 2] cycloaddition of the alkene and a ketene in a conjugated dienyl ketene to give a benzvalenone paddalane intermediate. Copyright
Selective Reduction of Carboxylic Acids to Alcohols in the Presence of Alcohols by a Dual Bulky Transition-Metal Complex/Lewis Acid Catalyst
Gr?mer, Bendik,Saito, Susumu,Yoshioka, Shota
, p. 1957 - 1964 (2022/02/10)
Here, we report a molecular method for the generally applicable reduction of mono-and dicarboxylic acids that selectively furnishes a diverse variety of alcohols, including mono-and diols. One of the inherent drawbacks of the direct hydrogenation of carboxylic acids to alcohols is the in situ formation of the corresponding esters via condensation of the carboxylic acids with the produced alcohols. Especially, the hydrogenation of polycarboxylic acids frequently suffers from the formation of a complex mixture of oligomeric esters. This issue was successfully overcome by the combined use of a dual catalyst that consists of a bulky (PNNP)iridium complex and a Lewis acid. Owing to the steric bulk and robustness of the iridium catalyst, the main role of the Lewis acid is to independently catalyze the esterification, albeit the cooperative activation of (a resting state of) the iridium catalyst by the Lewis acid also seems to be implied.
METABOLICALLY STABLE PRODRUGS
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Paragraph 00119, (2020/01/24)
Provided are prodrugs of various therapeutic agents that provide enhanced bioavilabilty of the therapeutic agent, and methods of treatment conditions in a subject by administration of the one or prodrugs. As provided herein a prodrug includes a therapeutic agent covalently attached to a cap, the cap having a structure according to formula (I) where: R1 is a branched or linear substituted or unsubstituted C2-C6 alkyl, alkenyl, or alkynl; X is -S(0)2-; R2 is a branched or linear substituted or unsubstituted C4-C20 alkyl, alkenyl, or alkynyl; and R3 is -H, C3-C5 cycloalkyl, C3-C5 cycloheteroalkyl, -C(CH3)3, -CF3, -C(CF3)3, or a substituted or unsubstituted phenyl.
Chemical synthesis of diglucosyl diacylglycerols utilizing glycosyl donors with stereodirecting cyclic silyl protective groups
Takato, Koichi,Kurita, Motoki,Yagami, Nahoko,Tanaka, Hide-Nori,Ando, Hiromune,Imamura, Akihiro,Ishida, Hideharu
, (2019/08/01)
Chemical syntheses of the bacterial diglucosyl diacylglycerols 1-heptadecanoyl-2-pentadecanoyl-3-O-[6-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl]-sn-glycerol and 1-(cis-13-octadecenoyl)-2-palmitoyl-3-O-[2-O-(α-d-glucopyranosyl)-α-d-glucopyranosyl]-sn-glycerol are described. The syntheses feature the stereoselective construction of glycosidic linkages in glycosylation reaction by utilizing glycosyl donors with stereodirecting cyclic silyl protective groups. The 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TIPDS) group was used for formation of the β-glycosidic linkage, while the di-tert-butylsilylene (DTBS) group was used for α-linkage formation. The silyl protective groups were chemoselectively cleavable without affecting acyl functionalities on the glycerol moiety and proved effective for the synthesis of diacylglycoglycerolipids.