72623-22-4Relevant academic research and scientific papers
Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0-Catalyzed Asymmetric C(sp3)-H Activation
Melot, Romain,Craveiro, Marcus V.,Bürgi, Thomas,Baudoin, Olivier
, p. 812 - 815 (2019)
A divergent enantioselective synthesis of (nor)illudalane sesquiterpenes was designed by using a Pd0-catalyzed asymmetric C(sp3)-H arylation as a key step to control the isolated, highly symmetric quaternary stereocenter of the targe
Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP
Tang, Shuang-Qi,Bricard, Jacques,Schmitt, Martine,Bihel, Frédéric
supporting information, p. 844 - 848 (2019/01/30)
An efficient and user-friendly palladium(II) precatalyst, POxAP (post-oxidative-addition precatalyst), was identified for use in Fukuyama cross-coupling reactions. Suitable for storage under air, the POxAP precatalyst allowed reaction between thioesters and organozinc reagents with turnover numbers of ～90000. A series of 23 ketones were obtained with yields ranging from 53 to 99%. As proof of efficacy, an alternative approach was developed for the synthesis of a key precursor of the natural product isoprekinamycin.
Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp3)-H Activation Strategy
Melot, Romain,Craveiro, Marcus V.,Baudoin, Olivier
, p. 12933 - 12945 (2019/08/20)
Three (nor)illudalane sesquiterpenes were synthesized from a common intermediate in racemic and enantioenriched forms using Pd0-catalyzed C(sp3)-H arylation as a key step. The configuration of the isolated, highly symmetric quaternar
Synthetic Study on Acremoxanthone A: Construction of Bicyclo [32.2]nonane CD Skeleton and Fusion of AB Rings
Hirano, Yoichi,Tokudome, Kensei,Takikawa, Hiroshi,Suzuki, Keisuke
supporting information, p. 214 - 220 (2017/01/25)
Toward the total synthesis of acremoxanthone A, a model study has revealed a convergent approach to construct the ABCDE ring system. The key steps include: (1) an effective construction of the bicyclo[3.2.2]nonane skeleton, (2) protocol for generating the bridgehead anion and trapping, and (3) 1,3-dipolar cycloaddition of a nitrile oxide to the internal alkene.
Construction of quaternary centres for natural polycycles: The Pauson-Khand approach
Arnáiz, Eduardo,Blanco-Urgoiti, Jaime,Abdi, Delbrin,Domínguez, Gema,Castells, Javier Pérez
, p. 2431 - 2437 (2008/09/20)
Construction of quaternary carbons is a challenge in PK chemistry, with few precedents in the literature. Starting from suitable functionalized enynes including an aromatic ring that templates the reaction, polycyclic ketones are obtained with a quaternar
Studies on the Synthesis of Substituted Phenanthrenoids
Leed, Andrew R.,Boettger, Susan D.,Ganem, Bruce
, p. 1098 - 1106 (2007/10/02)
Highly regioselective reactions for the construction of polysubstituted benzenes 18, 19, 20, 22, 24, and 44-47 are described, including some remarkable site-selective halogenations.These have been employed in the synthesis of halo-, nitro-, amino-, and urethane-substituted stilbenes 37, 38, and 51-56.Ideas for thermal as well as photochemical cyclizations are presented and explored.Stilbene 54 led to the formation of phenanthrenes 57, 58, and 62; likewise 55 furnished two new tricyclics, 60 and 61, whereas irradiation of 52 in tert-butylalcohol captured solvent to produce phenanthrenes 63 and 64.Strategies for the total synthesis of juncusol (1), a cytotoxic phytoalexin, are considered.
