72054-82-1Relevant academic research and scientific papers
Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin
Lei, Xiaoguang,Johnson, Richard P.,Porco Jr., John A.
, p. 3913 - 3917 (2003)
The [4+2] dimerization of epoxyquinol 1 is rendered irreversible by formation of a hemiacetal in the enantioselective total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin (2).
Synthesis of (+)-Antroquinonol and Analogues by Using Enantioselective Michael Reactions of Benzoquinone Monoketals
Hsu, Che-Sheng,Fang, Jim-Min
, p. 3809 - 3816 (2016/08/16)
(+)-Antroquinonol is an anticancer agent that was first isolated from the rare mushroom Antrodia cinnamomea, which is indigenous to Taiwan. In this study, (+)-antroquinonol is synthesized from benzoquinone monoketals by using an enantioselective Michael r
Direct synthesis of anilines and nitrosobenzenes from phenols
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
, p. 5520 - 5524 (2016/07/06)
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
Efficient Coupling Reaction of Quinone Monoacetal with Phenols Leading to Phenol Biaryls
Kamitanaka, Tohru,Morimoto, Koji,Tsuboshima, Kohei,Koseki, Daichi,Takamuro, Hitoho,Dohi, Toshifumi,Kita, Yasuyuki
supporting information, p. 15535 - 15538 (2016/12/09)
A simple and efficient synthesis of phenol biaryls by the cross-couplings of quinone monoacetals (QMAs) and phenols is reported. The Br?nsted acid catalytic system in 1,1,1,3,3,3-hexafluoro-2-propanol was found to be particularly efficient for this transformation. This reaction can be extended to the synthesis of various phenol biaryls, including sterically hindered biaryls, with yields ranging from 58 to 90 % under mild reaction conditions and in a highly regiospecific manner.
Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride
Yin, Zhiwei,Zhang, Jinzhu,Wu, Jing,Green, Riana,Li, Sihan,Zheng, Shengping
supporting information, p. 2854 - 2858 (2014/05/06)
An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent. This journal is the Partner Organisations 2014.
Sporolide B: Synthetic studies
Gladding, Jeffery A.,Bacci, James P.,Shaw, Scott A.,Smith III, Amos B.
scheme or table, p. 6697 - 6706 (2011/10/01)
Studies directed toward the synthesis of the architecturally complex marine natural product sporolide B are described. Synthetic analysis suggested advanced hydroquinone and benzodiquinane fragments, which upon elaboration were successfully united via an
A double oxidation procedure for the preparation of halogen-substituted para-benzoquinone monoketals: Asymmetric synthesis of (-)-harveynone
Hookins, Daniel R.,Taylor, Richard J.K.
experimental part, p. 6619 - 6621 (2011/02/21)
The double oxidation of halophenols with hypervalent iodine reagents in methanol provides a simple procedure to prepare halo-1,4-benzoquinone monoketals. Seven examples of this procedure are reported as is the conversion of 3-iodo-4,4-dimethoxycyclohexa-2
Synthesis of bromoxone
Gautier, Elisabeth C. L.,Lewis, Norman J.,McKillop, Alexander,Taylor, Richard J. K.
, p. 8759 - 8760 (2007/10/02)
A short synthetic route to the natural product bromoxone is reported (5 steps, 15% overall yield), involving regioselective monoepoxidation of an electrolytically-derived quinone monoketal followed by stereoselective ketone reduction.
An efficient, simple and inexpensive method for the preparation of 1,4-benzoquinone monoketals via anodic oxidation of 1,4-dimethoxybenzenes
Gautier,Lewis,McKillop,Taylor
, p. 2989 - 3008 (2007/10/02)
Anodic oxidation of a series of 1-substituted-2,5-dimethoxybenzenes gives 2-substituted-1,1,4,4-tetramethoxycyclohexa-2,5-dienes in almost quantitative crude yield. Selective monohydrolysis of these bis-ketals is possible in many cases, and gives 3-substi
