Ishikawa, Sekiha; Masuyama, Yoshikazu; Adachi, Takeshi; Shimonishi, Takeshi; Morimoto, Shotaro; Tanabe, Yoo published an article in 2021. The article was titled 《Synthesis of Naphthaleman Family Utilizing Regiocontrolled Benzannulation: Unique Molecules Composed of Multisubstituted Naphthalenes》, and you may find the article in ACS Omega.Category: bromides-buliding-blocks The information in the text is summarized as follows:
The naphthaleman family, a set of uniquely designed visual mol. structures comprising multisubstituted naphthalenes, I, wherein Yn = H, OMe, 3,4,5-(OMe)3, 1-naphthyl, was synthesized utilizing regiocontrolled benzannulation as a key step. The naphthaleman family possesses a common naphthalene body with a head comprising the 3,4-methylenedioxy group, sym. or unsym. right and left arms, and two alkynyl legs. The synthesis involves six C-C bond-forming reaction sequences. (i) syn-Stereoselective gem-dichlorocyclopropanation of Me angelate (86%). (ii) Acylation with ArMgBr (three examples, 60-91% yield). (iii) Stereocontrolled introduction of the 3,4-methylenedioxyphenyl group (three examples, 67-92% yield). (iv) Crucial regiocontrolled benzannulation to construct a common body segment (71-73% yield). (v) Two Suzuki-Miyaura cross-couplings to install the right or left arms (first-stage route: four examples, 77-93% and second-stage route: four examples, 42-90% yield). (vi) Double alkynylation to insert two legs (first-stage route: four examples, 61-77% yield and second-stage route: sole example, 83% yield). The four core members were produced through both first-stage and second-stage routes, with the second-stage approach demonstrating superiority over the first-stage approach. One of the members was alternatively synthesized by switching the installation order of the right and left arms, and identical twin members were produced by high-performance liquid chromatog. chiral separation The most stable conformations of two naphthaleman family members were calculated by Spartan software. In the part of experimental materials, we found many familiar compounds, such as 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Category: bromides-buliding-blocks)
1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.Category: bromides-buliding-blocks1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize analogs of HA14-1, which shows promising anticancer properties.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary