53167-11-6Relevant articles and documents
Synthesis of a truncated tetradenolide
Dávila García, álvaro,Bernès, Sylvain,Sartillo-Piscil, Fernando,Meza-León, Rosa Luisa
, p. 4373 - 4379 (2020)
The enantiopure synthesis of a truncated tetradenolide is presented. Starting from the versatile Chiron 7,3-lactone-xylofuranose derivative (7,3-LXF), the enantiomerically pure synthesis of the title compound is obtained in six steps with a 40% overall yield.
Synthesis and biological evaluation of 1,5-dideoxy-1,5-iminoxylitol-Aamino acid hybrids as xylosidase inhibitors
Steiner, Andreas J.,Stuetz, Arnold E.,Tarling, Chris A.,Withers, Stephen G.,Wrodnigg, Tanja M.
, p. 553 - 557 (2009)
1,5-Dideoxy-1,5-iminoxylitolamino acid hybrids have been synthesized by cyclisation via a double reductive amination of xylo-pentodialdose and the respective amino groups of lysine as well as serine components. Further modification with aromatic substituents gave access to lipophilic derivatives. Kinetic studies revealed that all compounds exhibited better inhibitory properties against β-xylosidase from Thermoanaerobacterium sacharolyticum than the parent iminosugar.
Asymmetric synthesis and biological evaluation of (+)-cardiobutanolide, (?)-3-deoxycardiobutanolide and analogues as antiproliferative agents
Kova?evi?, Ivana,Kesi?, Jelena,Popsavin, Mirjana,Francuz, Jovana,Koji?, Vesna,Jakimov, Dimitar,Rodi?, Marko V.,Zelenovi?, Bojana Sre?o,Benedekovi?, Goran,Popsavin, Velimir
supporting information, (2021/08/30)
Two natural products, (+)-cardiobutanolide and (?)-3-deoxycardiobutanolide, as well as five new analogues, were synthesized in several steps that included zinc-mediated THF ring opening, subsequent stereoselective olefination, and final Sharpless asymmetric dihydroxylation. In vitro antitumour activities of these compounds were evaluated against a panel of eight human tumour cell lines and one normal cell line. Some of compounds displayed powerful effects against tumour cells, but none of them were active toward normal cells. A SAR study revealed that the change of configuration at the C-6 and C-7 position of (+)-cardiobutanolide decreases antitumour activity of analogues. It also appears that the presence of a hydroxyl group at the C-3 position increases the activity of this type of lactones. A comparison of activities of conformationally rigid lactone goniofufurone with that of more flexible cardiobutanolide and 3-deoxycardiobutanolide indicates that steric flexibility has a positive effect on cytotoxicity. It was also confirmed that removal of the phenyl group may result in analogues of higher activity. Flow cytometry analysis revealed that the synthesized compounds did not induce apoptosis and necrosis of K562 cells. However, Western blot analysis showed that all compounds but one had an increased Bax/Bcl-2 protein expression ratio.
Method for preparing eribulin and intermediate thereof
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Paragraph 0128-0130, (2018/09/08)
The present invention relates to a method for preparing eribulin and an intermediate thereof. In particular, the invention relates to a method for preparing a compound of formula 5, R3 is selected from aldehyde or OR1, n=0 or 1, R1 is a hydroxy protecting group, and preferably the hydroxy protecting group is selected from tert-butyldimethylsilyl, tert-butyldiphenylsilyl, p-methoxybenzyl or benzyl.The invention also provides a method for preparing halichondrin and derivatives thereof such as the eribulin from the compound of formula 5.
Thermal and Lewis acid promoted intramolecular Diels-Alder reaction of furanose tethered 1,3,9-decatriene systems: A synthetic and computational investigation
Kalmode, Hanuman P.,Maity, Dilip K.,Bhate, Prakash M.
, p. 63445 - 63462 (2016/07/19)
The intramolecular Diels-Alder (IMDA) reaction of furanose tethered 1,3,9-decatrienes (4a-4r) was investigated under thermal conditions and in the presence of a Lewis acid. The stereoselectivity was determined by establishing the structures of adducts through single crystal X-ray diffraction and 1H NMR spectroscopy. It was found that contrary to expectations, the thermal IMDA reaction of (3E) and (3Z)-1,3,9-decatrienes proceeded with nearly equal rate and furnished IMDA adducts (6-25) with moderate stereoselectivity. In some cases, rearranged products (9, 12, 17 and 24) arising out of a 1,5-sigmatropic shift, cis-trans isomerization followed by IMDA reaction were formed. In contrast, a Lewis acid promoted IMDA reaction afforded only one adduct albeit in lower yields. Not surprisingly, cis-boat transition states were favored over trans-boat transition states. Experimental results were corroborated with transition state modeling of these reactions by applying density functional theory based electronic structure calculations.
General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses
Mulani, Shaheen K.,Cheng, Kuang-Chun,Mong, Kwok-Kong T.
supporting information, p. 5536 - 5539 (2015/12/01)
A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study
Benedekovi?, Goran,Francuz, Jovana,Kova?evi?, Ivana,Popsavin, Mirjana,Sre?o Zelenovi?, Bojana,Koji?, Vesna,Bogdanovi?, Gordana,Divjakovi?, Vladimir,Popsavin, Velimir
supporting information, p. 449 - 458 (2014/07/07)
Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres
Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes
O?a, Noe,Romero-Carrasco, Antonio,Pino-González, M. Soledad
, p. 156 - 163 (2013/04/10)
Epoxyamides obtained from d-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was
Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues
Hager, Dominik,Paulitz, Christian,Tiebes, Joerg,Mayer, Peter,Trauner, Dirk
, p. 10784 - 10801 (2013/11/19)
The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful strategy benefits from a variety of reagent-controlled stereoselective transformations, including a surprisingly facile and highly diastereoselective N-glycosylation process. The presented work also describes new building blocks that might find further application in carbohydrate chemistry.
Lewis acid-assisted olefin cross-metathesis reaction: An efficient approach for the synthesis of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin and evaluation of their antitumor activity
Nagarapu, Lingaiah,Gaikwad, Hanmant K.,Bantu, Rajashaker,Ganesh Kumar,Pombala, Sujitha
supporting information; scheme or table, p. 1287 - 1291 (2012/03/27)
A series of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin (2a-g) were synthesized via Lewis acid-assisted olefin cross-metathesis reaction using Ti(OiPr)4 30 mol % and 10 mol % of Grubb's second generation catalyst with good to excellent yields. Most of these compounds exhibited significant growth inhibitory effects on all the tested cancer cell lines and three compounds (2c, 2d and 2e) showed potent cytotoxic activity.