325172-28-9Relevant academic research and scientific papers
Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers
Chen, Dake,Berhane, Ilyas A.,Chemler, Sherry R.
supporting information, p. 7409 - 7414 (2020/06/29)
The copper-catalyzed enantioselective intramolecular hydroalkoxylation of unactivated alkenes for the synthesis of tetrahydrofurans, phthalans, isochromans, and morpholines from 4- and 5-alkenols is reported. The substrate scope is complementary to existing enantioselective alkene hydroalkoxylations and is broad with respect to substrate backbone and alkene substitution. The asymmetric induction and isotopic labeling studies support a polar/radical mechanism involving enantioselective oxycupration followed by C-[Cu] homolysis and hydrogen atom transfer. Synthesis of the antifungal insecticide furametpyr was accomplished.
Regiospecific ortho-C?H Allylation of Benzoic Acids
Trita, A. Stefania,Biafora, Agostino,Pichette Drapeau, Martin,Weber, Philip,Goo?en, Lukas J.
supporting information, p. 14580 - 14584 (2018/03/13)
A carboxylate-directed ortho-C?H functionalization has been developed and it allows the regiospecific introduction of allyl residues to benzoic acids. In the presence of a [Ru(p-cymene)Cl2]2 and K3PO4, benzoic acids react with allyl acetates at only 50 °C to give the corresponding ortho-allylbenzoic acids. The protocol is generally applicable to both electron-rich and electron-poor benzoic acids in combination with linear and branched allyl acetates. The products can be further functionalized in situ, for example, by double-bond migration, lactonization, or decarboxylation.
Catalytic C-N and C-H Bond Activation: Ortho-Allylation of Benzoic Acids with Allyl Amines
Hu, Xiao-Qiang,Hu, Zhiyong,Zhang, Guodong,Sivendran, Nardana,Goo?en, Lukas J.
supporting information, p. 4337 - 4340 (2018/07/29)
A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
Synthesis and structure-activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs
Garcia-Rodriguez, Jose,Mendiratta, Saurabh,White, Michael A.,Xie, Xiao-Song,De Brabander, Jef K.
supporting information, p. 4393 - 4398 (2015/10/12)
An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents.
Rhenium-catalyzed allylation of C-H bonds of benzoic and acrylic acids
Kuninobu, Yoichiro,Ohta, Kazuhiro,Takai, Kazuhiko
supporting information; experimental part, p. 10791 - 10793 (2011/11/05)
We have succeeded in the allylation of aromatic and olefinic C-H bonds of benzoic and acrylic acids using a rhenium catalyst, Re2(CO) 10. In this reaction, isomerization of the introduced allyl group to the 1-propenyl group did not occur.
Stereoselective Formal Synthesis of (-)-Salicylihalamides A and B Via Prins Cyclisation
Yadav,Venkateswar Rao,Purushothama Rao,Sridhar Reddy,Prasad
scheme or table, p. 457 - 460 (2011/09/14)
A stereoselective and convergent formal approach to Salicylihalamide A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion and ring closing metathesis along with Prins cyclisation.
Synthesis and cytotoxicity of a salicylihalamide a analogue
Tang, Shaoshan,Erickson, Karen L.
supporting information; experimental part, p. 898 - 901 (2009/04/05)
The synthesis of a simple analogue of salicylihalamide A with a truncated lactone ring (±2) was achieved in 10 steps. Its cytotoxicity profile in the NCI 60-cell-line human tumor assay differed significantly from that of salicylihalamide A in both level a
First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation
Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
, p. 3419 - 3429 (2008/02/03)
(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).
Directed ortho-metalation of unprotected benzoic acids. Methodology and regioselective synthesis of useful contiguously 3- and 6-substituted 2-methoxybenzoic acid building blocks
Nguyen, Thi-Huu,Castanet, Anne-Sophie,Mortier, Jacques
, p. 765 - 768 (2007/10/03)
By treatment with s-BuLi/TMEDA at -78 °C, unprotected 2-methoxybenzoic acid is deprotonated exclusively in the position ortho to the carboxylate. A reversal of regioselectivity is observed when the acid is treated with n-BuLi/t-BuOK. These results are of general utility for the one-pot preparation of a variety of very simple 3- and 6-substituted 2-methoxybenzoic acids that are not easily accessible by conventional means. The potential usefulness of the method is demonstrated by the expedient synthesis of lunularic acid.
Formal total synthesis of (-)-salicylihalamides A and B
Yadav,Srihari
, p. 81 - 89 (2007/10/03)
Formal total synthesis of (-)-salicylihalamides A and B is described starting with a nonracemic chiral epoxide obtained from Jacobsen's kinetic resolution. Sharpless asymmetric epoxidation, Diels Alder reaction, Mitsunobu coupling and ring closing metathe
