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.
Facile preparation of 2-arylbenzo[b]furan molecules and their anti-inflammatory effects
Hwang, Jung Woon,Choi, Da Hye,Jeon, Jae-Ho,Kim, Jin-Kyung,Jun, Jong-Gab
experimental part, p. 965 - 970 (2010/11/02)
An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.
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.
Total synthesis of ailanthoidol and precursor XH14 by stille coupling
Lin, Shun-Yu,Chen, Chih-Lung,Lee, Yean-Jang
, p. 2968 - 2971 (2007/10/03)
Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the
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.
A convenient synthesis of naturally occurring benzofuran ailanthoidol
Kao, Chai-Lin,Chern, Ji-Wang
, p. 1111 - 1113 (2007/10/03)
A convenient method for the synthesis of ailanthoidol starting from vanillin is provided using trimethylsilyldiazomethane lithium salt to generate a diphenylacetylene and subsequent oxymercuration cyclization of the resulting alkyne with mercury acetate in acetic acid as key steps.
A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan
Fuganti, Claudio,Serra, Stefano
, p. 5609 - 5610 (2007/10/03)
A general method of synthesis of 2-aryl-7-alkoxy-benzofurans is described using a benzoannulation reaction as key step. The usefulness of this approach is shown in the new synthesis of ailanthoidol, a benzofuranoid neolignan isolated from the tree Zanthox
Synthesis of natural products possessing a benzo[b]furan skeleton
Luetjens, Henning,Scammells, Peter J.
, p. 6581 - 6584 (2007/10/03)
A related synthetic strategy has been used to prepare two natural products XH-14 and ailanthoidol) which possess a benzo[b]furan skeleton. The synthesis of XH-14 involved the use of a palladium-catalyzed cyclization with concomitant carbonylation via insertion of carbon monoxide to introduce regioselectively a formyl group in the 3-position.
