26908-23-6Relevant academic research and scientific papers
A concise asymmetric total synthesis of (+)-brevisamide
Herrmann, Aaron T.,Martinez, Steven R.,Zakarian, Armen
, p. 3636 - 3639 (2011)
A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A pen
Photo-oxidation of 2-furyl-alkyl-phosphonates: Synthesis of new cyclopentenone derivatives
D'Onofrio, Franco,Piancatelli, Giovanni,Nicolai, Massimo
, p. 4083 - 4088 (1995)
The furan ring in the title compounds was opened with singlet oxygen in methanol. New phosphonate cyclopentenone derivatives were synthesized.
The furan approach to azacyclic compounds
García, Isela,Pérez, Manuel,Gándara, Zoila,Gómez, Generosa,Fall, Yagamare
, p. 3609 - 3612 (2008)
We describe an efficient new approach to the synthesis of azacyclic compounds that extends our recently developed methodology based on the oxidation of a furan ring with singlet oxygen followed by an intramolecular hetero Michael addition. The new approac
The furan approach to thiacyclic compounds. Stereoselective synthesis of 2,3-disubstituted tetrahydrothiopyrans
Boullosa, Seila,Gándara, Zoila,Pérez, Manuel,Gómez, Generosa,Fall, Yagamare
, p. 4040 - 4042 (2008)
We describe an efficient new approach to the synthesis of thiacyclic compounds that extends the methodology we previously developed for oxacycles: oxidation of a furan ring with singlet oxygen, followed by intramolecular hetero Michael addition. The new a
Strain-activated diels-alder trapping of 1,2-cyclohexadienes: Intramolecular capture by pendent furans
Lofstrand, Verner A.,McIntosh, Kyle C.,Almehmadi, Yaseen A.,West
, p. 6231 - 6234 (2019)
Intramolecular [4 + 2] cycloaddition reactions of substituted 1,2-cyclohexadienes with pendent furans enables the synthesis of complex tetracyclic scaffolds in a single step under mild conditions. All Diels-Alder cycloadducts were obtained as single diast
Synthesis and Biological Evaluation of Dimeric Furanoid Macroheterocycles: Discovery of New Anticancer Agents
Nicolaou,Nilewski, Christian,Hale, Christopher R. H.,Ahles, Christopher F.,Chiu, Chiao An,Ebner, Christian,Elmarrouni, Abdelatif,Yang, Lifeng,Stiles, Katherine,Nagrath, Deepak
, p. 4766 - 4770 (2015)
A recently developed dimerization/macrocyclization was employed to synthesize a series of macroheterocycles which were biologically evaluated, leading to the discovery of a number of potent cytotoxic agents (e.g., 27: GI50 = 51 nM against leukemia CCRF-CEM cell line; 29: GI50 = 99 nM against melanoma MDA-MB-435 cell line). Further biological studies support an apoptosis mechanism of action for these compounds involving deregulation of the tricarboxylic acid cycle activity and suppression of mitochondrial function in cancer cells. (Chemical Equation Presented).
Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2
Xing, Qingzhao,Hao, Zhe,Hou, Jing,Li, Gaoqiang,Gao, Ziwei,Gou, Jing,Li, Chaoqun,Yu, Binxun
, p. 9563 - 9586 (2021/07/20)
Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.
Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride
Gu, Yiting,Lisnyak, Vladislav G.,Norton, Jack R.,Salahi, Farbod,Snyder, Scott A.,Zhou, Zhiyao
supporting information, p. 9657 - 9663 (2021/07/19)
Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.
Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
Aleku, Godwin A.,Leys, David,Roberts, George W.
, p. 3927 - 3939 (2020/07/09)
We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water
Luo, Nianhua,Liao, Jianhua,Ouyang, Lu,Wen, Huiling,Liu, Jitian,Tang, Weiping,Luo, Renshi
, p. 3025 - 3031 (2019/08/30)
The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.
