353-54-8Relevant academic research and scientific papers
Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Che, Chi-Ming,Wu, Kai,Wu, Liang-Liang,Zhou, Cong-Ying
supporting information, p. 16202 - 16208 (2020/07/17)
A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
Concise and practical approach for the synthesis of honokiol, a neurotrophic agent
Khan, P. Rasvan,Mujawar, Taufiqueahmed,Shankar, G.,Shekhar, P.,Subba Reddy, BV.,Subramanyam, Ravi
supporting information, (2020/08/06)
An improved method has been developed for the synthesis of honokiol using a readily available p-bromophenol as a precursor. The key step involved in this method is ortho-lithiation facilitated by methoxymethyl ether (MOM). Other important steps are ortho-allyl phenyl ether Claisen rearrangement and a Suzuki coupling for the construction of biaryls. This method does not require pre-functionalization of aromatic ring with bromide for the generation of arylboronic acid.
(NHC)AgCl catalyzed bromofluorocyclopropanation of alkenes with CFBr2CO2Na
Andrianova, Anastasia A.,Maslova, Yulia D.,Novikov, Maxim A.,Semenov, Sergei E.,Nefedov, Oleg M.
, p. 49 - 55 (2018/03/08)
An effective method for bromofluorocyclopropanation of electron-rich (aryl substituted), electron-neutral (monoalkyl substituted), electron-poor (haloalkenes, allylic esters, α,β-unsaturated esters) and acid/base sensitive silyl- and boronyl substituted a
SYNTHESIS OF HONOKIOL
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, (2017/06/01)
Disclosed herein are improved methods for the synthesis of honokiol, as well as methods for the synthesis of 3,3′-di-tert-butyl-5,5′-dimethyl-[1,1′-biphenyl]-2,4′-diol, 3′,5-dimethyl-[1,1′-biphenyl]-2,4′-diol, and 2,4′-dimethoxy-3′,5-dimethyl-1,1′-biphenyl, 3,3′,5,5′-tetra-tert-butyl-[1,1′-biphenyl]-2,4′-diol, and certain tetrasubstituted bisphenols, and uses therefor.
Total synthesis of honokiol by selective samarium-mediated allylic benzoate reduction
Wright, Alicia M.,O'Neil, Gregory W.
, p. 3441 - 3443 (2016/07/18)
The total synthesis of the biologically relevant compound honokiol has been completed featuring a samarium-mediated bis-benzoyl ester reduction to simultaneously install both allyl substituents found in the natural product. This reaction was performed after a Suzuki coupling was used to generate the biphenyl core, thereby avoiding problems associated with the acidity of these allyl groups and their propensity to isomerize. In this way, the synthesis of honokiol could be completed in 4 steps and 42% overall yield.
Efficient synthesis of neurotrophic honokiol using Suzuki-Miyaura reactions
Harada, Kenichi,Arioka, Chiharu,Miyakita, Akina,Kubo, Miwa,Fukuyama, Yoshiyasu
, p. 6001 - 6003 (2014/12/11)
Efficient synthesis of honokiol (1) was accomplished using two kinds of Suzuki-Miyaura reactions. The first Suzuki-Miyaura reaction was employed to couple 2-bromophenol (6) with 4-hydroxyphenylboronic acid (5), giving rise to biphenol 4, and the second co
Concise total synthesis of honokiol via Kumada cross coupling
Srinivas, Jada,Singh, Parvinder Pal,Varma, Yogesh Kumar,Hyder, Irfan,Kumar, Halmuthur M. Sampath
, p. 4295 - 4297 (2014/07/22)
A concise four-step efficient synthesis of honokiol 1 in 68% overall yield is described here. The present method involves tetrakis(triphenylphosphine) palladium [Pd(Ph3)4] catalyzed Kumada coupling in two key steps. First coupling generates biaryl backbone intermediate 5 and second generates 2,4′-O-dimethylhonokiol 3. Final demethylation under AlCl 3/DMS condition affords honokiol in quantitative yield.
A short and efficient synthesis of honokiol via Claisen rearrangement
Subba Reddy,Nageshwar Rao,Siva Senkar Reddy,Somaiah,Yadav,Subramanyam, Ravi
, p. 1049 - 1051 (2014/02/14)
A concise and efficient total synthesis of honokiol, a biphenyl-type neolignan is accomplished in six steps using readily available and cost-effective reagents. The synthetic route involves mainly the Grignard reaction, iodine mediated aromatization, and Claisen rearrangement as key steps. A predominant formation of honokiol (1a) was observed in the Claisen rearrangement under microwave irradiation whereas the isohonokiol (1b) was formed as a major product under conventional conditions.
A short and efficient synthesis of honokiol via Claisen rearrangement
Subba Reddy,Nageshwar Rao,Siva Senkar Reddy,Somaiah,Yadav,Subramanyam, Ravi
, p. 1049 - 1051 (2015/02/19)
A concise and efficient total synthesis of honokiol, a biphenyl-type neolignan is accomplished in six steps using readily available and cost-effective reagents. The synthetic route involves mainly the Grignard reaction, iodine mediated aromatization, and Claisen rearrangement as key steps. A predominant formation of honokiol (1a) was observed in the Claisen rearrangement under microwave irradiation whereas the isohonokiol (1b) was formed as a major product under conventional conditions.
