- Modular and Divergent Syntheses of Protoberberine and Protonitidine Alkaloids
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A modularly convergent and divergent strategy was established for the family synthesis of both protoberberine and protonitidine alkaloids. The robust, scalable, and flexible synthetic route featured a collective preparation of protoberberine and protonitidine alkaloids from a common isoquinoline assembled from pyridyne as the key synthon, which was based on the selective N-C or C-C cyclization via distinct processes. Through the strategy, 20 protoberberine alkaloids, 5 protonitidine alkaloids, and 11 analogues with diverse substituents were comprehensively aquired.
- Liu, Kai,Jiang, Xuefeng
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supporting information
p. 1327 - 1332
(2021/03/03)
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- Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
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A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
- Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
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supporting information
p. 14330 - 14334
(2020/10/12)
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- Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation
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A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.
- Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew
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p. 346 - 364
(2019/01/08)
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- Stereoselective synthesis of a: Podophyllum lignan core by intramolecular reductive nickel-catalysis
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A Ni-catalyzed reductive cascade to a diastereocontrolled construction of THN[2,3-c]furan, is developed. The mild reaction conditions led to the tolerance of broad functional groups that can be placed in almost every position of this skeleton with good yields. The conformational control for the observed trans- or cis-fused selectivity during this tandem cyclization-coupling is also proposed.
- Xiao, Jian,Cong, Xiao-Wei,Yang, Gui-Zhen,Wang, Ya-Wen,Peng, Yu
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supporting information
p. 2040 - 2043
(2018/03/01)
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- Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines
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A novel osmium-catalyzed cyclization of o-alkynyl phenethylamines to give 3-benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3-benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X-ray crystallography.
- álvarez-Pérez, Andrea,González-Rodríguez, Carlos,García-Yebra, Cristina,Varela, Jesús A.,O?ate, Enrique,Esteruelas, Miguel A.,Saá, Carlos
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supporting information
p. 13357 - 13361
(2015/11/09)
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- Aromatic iodination using N-iodosaccharin in room temperature ionic liquids
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More reactive iodination conditions have been developed that combine the use of room temperature ionic liquids with N-iodosaccharin. Using these reaction conditions, even very modestly activated arenes such as toluene can be iodinated in good yield under very mild conditions.
- Bailey, Lindsey,Handy, Scott T.
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experimental part
p. 2413 - 2414
(2011/05/09)
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- Osmium-catalyzed 7-endo heterocyclization of aromatic alkynols into benzoxepines
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[Figure Presented] The wizard of Os: Regioselective osmiumcatalyzed 7-endo heterocyclization of aromatic alkynols affords benzoxepines in good yields. The proposed catalytic cycle involves the key formation of osmiumvinylidene complexes via an alkynyl-hydride-osmium(IV) complex from the starting alkynol.
- Varela-Fernandez, Alejandro,Garcia-Yebra, Cristina,Varela, Jesus A.,Esteruelas, Miguel A.,Saa, Carlos
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supporting information; experimental part
p. 4278 - 4281
(2010/08/07)
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- An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation
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Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure h
- Ruiz, Javier,Ardeo, Ainhoa,Ignacio, Roberto,Sotomayor, Nuria,Lete, Esther
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p. 3311 - 3324
(2007/10/03)
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- Construction of the benzindenoazepine skeleton via cyclopentannulation of Fischer aminocarbene complexes: Total synthesis of bulgaramine
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A total synthesis of bulgaramine has been accomplished with a longest linear sequence of eight steps and an overall yield of 23% from commercially available 3,4-dimethoxyphenethyl alcohol. An intramolecular cyclopentannulation reaction of a Fischer aminoc
- Giese, Matthew W.,Moser, William H.
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p. 6222 - 6229
(2007/10/03)
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- Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes
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(Matrix presented) A variety of substituted naphthalenes have been prepared by the palladium-catalyzed carboannulation of internal alkynes. This method (1) forms two new carbon-carbon bonds in a single step, (2) accommodates a variety of functional groups
- Huang, Qinhua,Larock, Richard C.
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p. 2505 - 2508
(2007/10/03)
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