63604-94-4Relevant articles and documents
Synthesis of Ruscodibenzofuran (8-acetyl-7-hydroxy-1,4-dimethyldibenzofuran)
Scannell, Ralph T.,Stevenson, Robert
, p. 1103 - 1104 (1980)
A short synthesis of ruscodibenzofuran (1), a dibenzofuran extractive of Ruscus aculeatus, is described, the two significant steps of which exemplify a general route for the conversion of phenols into dibenzofurans.
Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
Deichert, Julie A.,Mizufune, Hideya,Patel, Jignesh J.,Hurst, Timothy E.,Maheta, Ashish,Kitching, Matthew O.,Ross, Avena C.,Snieckus, Victor
supporting information, p. 4693 - 4697 (2020/05/08)
The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction.
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
supporting information, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.