238434-65-6Relevant articles and documents
A novel and general synthetic pathway to strychnos indole alkaloids: Total syntheses of (-)-tubifoline, (-)-dehydrotubifoline, and (-)-strychnine using palladium-catalyzed asymmetric allylic substitution
Mori, Miwako,Nakanishi, Masato,Kajishima, Daisuke,Sato, Yoshihiro
, p. 9801 - 9807 (2003)
A method of palladium-catalyzed asymmetric allylic substitution for synthesizing 2-substituted cyclohexenylamine derivatives was established. Treatment of a 2-silyloxymethylcyclohexenol derivative with ortho-bromo-N-tosylaniline in the presence of Pd2dba 3·CHCl3 and (S)-BINAPO in THF afforded a cyclohexenylamine derivative with 84% ee in 80% yield. The Heck reaction was carried out to produce an indolenine derivative in good yield. Using this method, we synthesized indolenine derivative 7, which was recrystallized from EtOH to give an optically pure compound. From this compound, tetracyclic ketone 13, which should be a useful intermediate for the synthesis of indole alkaloids, could be synthesized. The total syntheses of (-)-dehydrotubifoline, (-)-tubifoline, and (-)-strychnine were achieved from 13. All ring constructions for the syntheses of these natural products were achieved using a palladium catalyst.
Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans
Hanessian, Stephen,Szychowski, Janek,Pablo Maianti
supporting information; experimental part, p. 429 - 432 (2009/09/25)
(Chemical Equation Presented) A synthesis of verdamicin C2 and its congener C2a has been accomplished from sisomicin relying on a novel oxidative transformation of an allylic azide to the corresponding α,β- unsaturated aldehyde, and its stereocontrolled elaboration into the intended 5′ side chain of verdamicin C2 and C2a. In vitro antibacterial testing shows that both C6′ epimers in verdamicin C2 and C2a are equally active against a variety of bacterial strains. Oxidation of allylic primary azides, ethers, and esters of 2-substituted dihydro[2H]pyrans with SeO2 leads directly to the corresponding aldehydes.