3772-55-2Relevant academic research and scientific papers
The microbiological transformation of the diterpenes dehydroabietanol and teideadiol by Mucor plumbeus
Fraga, Braulio M.,Hernandez, Melchor G.,Artega, Jose M.,Suarez, Sergio
, p. 663 - 668 (2003)
The microbiological transformation of dehydroabietanol (18-hydroxy-dehydroabietane) by Mucor plumbeus led to 2α,18-dihydroxy-abieta-8,11,13,15-tetraene, 2α,15-dihydroxy-dehydroabietanol, 2α-hydroxy-15-methoxy-dehydroabietanol, 7β-hydroxy-2-oxo-dehydroabietanol, 15-hydroxy-2-oxo-dehydroabietanol and 15,16-dihydroxy-2-oxo-dehydroabietanol, whilst that of teideadiol (1α,18-dihydroxy-dehydroabietane) gave 2α-hydroxy-teideadiol, 7α-hydroxy-teideadiol and 7β-hydroxy-teideadiol. Thus, 2α- and 7β-hydroxylation occur in both biotransformations and the 15-hydroxylation is inhibited in the biotransformation of teideadiol by the presence of a 1α-alcohol.
Ichthyotoxic sesterterpenoids from the New Guinean sponge Carteriospongia foliascens
Braekman,Daloze,Kaisin,Moussiaux
, p. 4603 - 4614 (1985)
Six 20,24-dimethylscalarane derivatives (5, 12, 15, 17, 19, and 21) have been isolated from the New Guinean sponge Carteriospongia foliascens. Compound 12 is identical with a C27 tetracyclic terpene previously isolated from an Australian specimen of the same sponge. The five other derivatives are new and their structures have been established on the basis of their spectral data. The structure of 5 was confirmed by single-crystal X-ray diffraction and that of 15 by chemical correlation with 12. The configuration at C-4 for all these compounds has been determined through 13C NMR data. Evidence leading to reverse the configuration at this centre in previously reported C27 tetracyclic terpenes is discussed. An ecological function is suggested for these molecules.
Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction
González-Cardenete, Miguel A.,Zaragozá, Ramón J.
, p. 15015 - 15022 (2020/04/27)
The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.
Late-stage C-H amination of abietane diterpenoids
Lapuh, María Ivana,Dana, Alejandro,Di Chenna, Pablo H.,Darses, Benjamin,Durán, Fernando J.,Dauban, Philippe
, p. 4736 - 4746 (2019/05/24)
This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.
Hydrogen Atom Transfer Induced Boron Retaining Coupling of Organoboronic Esters and Organolithium Reagents
Wang, Dinghai,Mück-Lichtenfeld, Christian,Studer, Armido
supporting information, p. 14126 - 14130 (2019/10/11)
α-Functionalization of alkyl boronic esters and homologation of aryl boronic esters by regioselective radical C(sp3)-H activation in boron-ate complexes is reported. Reaction of commercial or readily accessed aryl boronic acid pinacol esters with alkyl lithium reagents provides boron-ate complexes. Selective α-C-H abstraction by in situ generated trifluoromethyl radicals leads to radical anions that undergo electron transfer oxidation followed by 1,2-aryl/alkyl migration from boron to carbon to give the α-arylated/alkylated alkyl boronic esters. The valuable boronic ester functionality remains in the products and the cheap trifluoromethyl iodide acts as the oxidant in these C-C couplings. The 1,2-alkyl migration from boron to carbon is highly stereospecific allowing access to stereoisomerically pure boronic esters.
Oxidation of Tertiary Aromatic Alcohols to Ketones in Water
Chen, Dengfeng,Zhang, Yuchen,Pan, Xingyu,Wang, Fei,Huang, Shenlin
supporting information, p. 3607 - 3612 (2018/09/18)
A new rosin-based amphiphile enables the oxidation of tertiary aromatic alcohols in water under mild conditions. The oxidation process is mediated by β-scission of alkoxy radicals. Our catalyst system including the surfactant, catalysts, and water can be easily recycled within the same reaction vial. (Figure presented.).
A dehydrogenation fir acid derivative and its preparation method and application (by machine translation)
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Paragraph 0116; 0117; 0118; 0119, (2018/07/30)
The application relates to a dehydrogenation fir acid derivatives, the dehydroabietic acid derivatives preparation method and the dehydroabietic acid derivatives in the preparation of an anticancer drug. The application will be dehydroabietic acid carboxyl reduction dioxiding hydroxy, get the alcoholic hydroxy with anticancer activity of dehydroabietic acid derivatives. Then, to the alcoholic hydroxyl group as the starting compound dehydroabietic acid derivatives, the introduction of alkyl, acyl and aromatic sulfonyl and further improve the dehydroabietic acid derivatives of the anti-cancer activity. Beneficial effect of the application is characterized in that the elastomeric natural products, the raw materials used are non-toxic to the patient, and raw materials are easy, the price is cheap, simple method of synthesis of compounds, synthetic compounds obtainable by anticancer effect. (by machine translation)
Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes
Wang, Di,Xue, Xiao-Song,Houk, Kendall N.,Shi, Zhuangzhi
supporting information, p. 16861 - 16865 (2018/11/27)
The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.
Antiprotozoal activity of triazole derivatives of dehydroabietic acid and oleanolic acid
Pertino, Mariano Walter,Vega, Celeste,Rolón, Miriam,Coronel, Cathia,De Arias, Antonieta Rojas,Schmeda-Hirschmann, Guillermo
, (2017/03/15)
Tropical parasitic diseases such as Chagas disease and leishmaniasis are considered a major public health problem affecting hundreds of millions of people worldwide. As the drugs currently used to treat these diseases have several disadvantages and side effects, there is an urgent need for new drugs with better selectivity and less toxicity. Structural modifications of naturally occurring and synthetic compounds using click chemistry have enabled access to derivatives with promising antiparasitic activity. The antiprotozoal activity of the terpenes dehydroabietic acid, dehydroabietinol, oleanolic acid, and 34 synthetic derivatives were evaluated against epimastigote forms of Trypanosoma cruzi and promastigotes of Leishmaniabraziliensis and Leishmania infantum. The cytotoxicity of the compounds was assessed on NCTC-Clone 929 cells. The activity of the compounds was moderate and the antiparasitic effect was associated with the linker length between the diterpene and the triazole in dehydroabietinol derivatives. For the oleanolic acid derivatives, a free carboxylic acid function led to better antiparasitic activity.
Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid
Pertino, Mariano Walter,Verdugo, Valery,Theoduloz, Cristina,Schmeda-Hirschmann, Guillermo
, p. 2523 - 2535 (2014/03/21)
Dehydroabietic acid (DHA) is a naturally occurring diterpene with different and relevant biological activities. Previous studies have shown that some DHA derivatives display antiproliferative activity. However, the reported compounds did not include triazole derivatives. Starting from DHA (8,11,13-abietatrien-18- oic acid), and its alcohol dehydroabietinol (8,11,13-abietatrien-18-ol), four alkyl esters were prepared. The alkyl terpenes were treated with different aromatic azides to synthesize hybrid compounds using click chemistry. Some 16 new DHA hybrids were thus synthesized and their structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new compounds was assessed towards human cell lines, namely normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. Better antiproliferative effect was found for compound 5, with an IC50 of 6.1 μM and selectivity on SK-MES-1 cells. Under the same experimental conditions, the IC50 of etoposide, was 1.83 μM.
