90841-59-1Relevant articles and documents
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
, p. 14330 - 14334 (2020)
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.
Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids
Kapadia, Nirav,Harding, Wayne
supporting information, p. 8914 - 8920 (2013/09/23)
Oxa-Pictet-Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g]chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps.
Enantioselective total syntheses of cedrelin A and methylated paralycolin B using Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols
Suzuki, Yuta,Matsuo, Nobuaki,Nemoto, Tetsuhiro,Hamada, Yasumasa
, p. 5913 - 5919 (2013/07/27)
We report the first enantioselective total syntheses of cedrelin A and methylated paralycolin B, wherein Pd-catalyzed asymmetric intramolecular Friedel-Crafts allylic alkylation of phenols was the key step.
A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids
Pedrosa,Andres,Iglesias
, p. 243 - 250 (2007/10/03)
A novel, direct, and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes.
