213970-71-9Relevant articles and documents
Synthesis and Cytotoxicity Studies of Bioactive Benzofurans from Lavandula agustifolia and Modified Synthesis of Ailanthoidol, Homoegonol, and Egonol
Sivaraman, Aneesh,Kim, Jin Sook,Harmalkar, Dipesh S.,Min, Kyoung Ho,Park, Joong-Won,Choi, Yongseok,Kim, Kyungtae,Lee, Kyeong
, p. 3354 - 3362 (2020/11/23)
2-Aryl/alkylbenzofurans, which constitute an important subclass of naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted and tetrasubstituted benzofurans bearing the hydroxyethyl unit, including the natural compounds isolated from Lavandula agustifolia (1-3) and their non-natural derivatives (4-8), was accomplished. We also report a modified synthesis of ailanthoidol, homoegonol, and egonol that enables the divergent synthesis of their derivatives for future exploration. Among these, the representative phenolic natural compound 2 and its derivatives 7 and 5 induced apoptotic cell death related poly(ADP-ribose) polymerase (PARP) cleavage in MCF74, A549, PC3, HepG2, and Hep3B cancer cell lines. Additionally, the tumor suppressor protein p53 was also induced in p53 wild type cancer cells.
An expeditious and convergent synthesis of ailanthoidol
Rao, Maddali L.N.,Awasthi, Dheeraj K.,Banerjee, Debasis
experimental part, p. 1979 - 1981 (2010/06/21)
An expeditious and concise method has been described for the synthesis of ailanthoidol through convergent route starting from vanillin. The protocol involving intramolecular Wittig as a key reaction afforded ailanthoidol in overall high yield.
A novel strategy for the synthesis of benzofuran skeleton neolignans: Application to ailanthoidol, XH-14, and obovaten
Kao, Chai-Lin,Chern, Ji-Wang
, p. 6772 - 6787 (2007/10/03)
A convenient and general approach to the synthesis of the benzofuran skeleton compounds ailanthoidol, XH-14, and obovaten was developed. Starting from vanillin, a series of reactions afforded 7 in 71% yield. Treatment of 7 with n-BuLi followed by addition of substituted benzaldehydes resulted in the formation of carbinols 11 and 31. The substituted benzophenones obtained from oxidation of 11 and 31 were treated with trimethylsilyldiazomethane lithium salt to give diphenylacetylenes 15 and 33, respectively. 15 and 33 were then cyclized in the presence of either mercury acetate in acetic acid or bromine in chloroform to give 3-chloromercurio- or 3-bromobenzofuran, respectively. The 3-chloromercurio intermediates could be reduced to proton or derivatized to ester or bromide, leading to the synthesis of ailanthoidol, XH-14, and obovaten, respectively. In addition, necleophilic substitution was used to introduce a formyl or methyl group into the 3-bromobenzofuran derivatives, providing an alternative pathway to XH-14 and obovaten. The final elongation and deprotection reaction furnished the desired ailanthoidol, XH-14, and obovaten in yields of 30, 15, and 11%, respectively.
