- Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products
-
Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthesis of the complex taiwanschirin fused [8,6,5] core through a novel alkynylation reaction coupled with an intramolecular Heck reaction used to construct the 8-membered ring.
- Christensen, Kirsten E.,Donohoe, Timothy J.,Haughey, Maxwell B.,Poole, Darren L.
-
p. 13392 - 13397
(2021/11/01)
-
- Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement
-
The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.
- Feberero, Claudia,Lopez, Carlos Silva,Sanz, Roberto,Sedano, Carlos,Suarez-Pantiga, Samuel
-
p. 12561 - 12578
(2020/11/09)
-
- Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions
-
A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a
- Youn, So Won,Kim, Young Ho,Jo, Yoon Hyung
-
supporting information
p. 462 - 468
(2019/01/04)
-
- 1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement
-
The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.
- Feberero, Claudia,Suárez-Pantiga, Samuel,Cabello, Zaida,Sanz, Roberto
-
supporting information
p. 2437 - 2440
(2018/04/27)
-
- An Efficient and Modular Route to C 3?-TunePhos-Type Ligands
-
An efficient and modular synthetic route to the bidentate C 3?-TunePhos was developed, which allowed tunable steric and electronic effects of the ligands. This novel chemical technology highlights a versatile C 3?-dibromodiphenyl int
- Deng, Xu,Guan, Yu-Qing,Huo, Ning-Ning,Wang, Ya-Jing,Lv, Hui,Zhang, Xu-Mu
-
supporting information
p. 3726 - 3730
(2017/08/16)
-
- NEW BICYCLIC DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
-
Compounds of formula (I); wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, W, A and n are as defined in the description. Medicaments.
- -
-
Page/Page column 95
(2017/05/12)
-
- Regioselectivity of Diels-Alder reactions between 6,7-dehydrobenzofuran and 2-substituted furans
-
We describe the first report of the generation of 6,7-dehydrobenzofuran(6, 7-benzofuranyne) from 6,7-dihalobenzofurans via metal-halogen exchange and elimination, in a manner similar to our previous work with 6,7-indole arynes. This benzofuranyne undergoe
- Brown, Neil,Buszek, Keith R.
-
experimental part
p. 4022 - 4025
(2012/08/28)
-
- 5-MEMBERED HETEROARYL DERIVATIVES USED AS SPHINGOSINE 1-PHOSPHATE RECEPTOR AGONISTS
-
5-membered heteroaryl derivatives of formula (I) or salts thereof, processes for their preparation, pharmaceutical compositions containing them and their uses in the treatment of various disorders mediated by S1P1 receptors are disclosed.
- -
-
Page/Page column 62-63
(2011/01/12)
-
- Axially chiral electron-rich TunePhos-type ligand: synthesis and applications in asymmetric hydrogenation
-
A new electron-rich TunePhos type ligand has been synthesized; excellent enantioselectivities (up to 99% ee) have been achieved in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid methyl esters and dimethyl itaconate.
- Zou, Yaping,Geng, Huiling,Zhang, Weicheng,Yu, Shichao,Zhang, Xumu
-
scheme or table
p. 5777 - 5779
(2009/12/26)
-
- A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols
-
Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc
- Sanz, Roberto,Castroviejo, M. Pilar,Fernandez, Yolanda,Fananas, Francisco J.
-
p. 6548 - 6551
(2007/10/03)
-