61654-73-7Relevant academic research and scientific papers
Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling
Mori, Atsunori,Morii, Kazuki,Morikawa, Daiki,Okano, Kentaro,Yasuda, Yuto
, p. 13388 - 13401 (2021/10/12)
A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at -78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide in the presence of catalytic palladium to provide the fully substituted pyrrole. Subsequent halogen-lithium exchange was performed to incorporate a boronate group exclusively at the β position proximal to the ester moiety. This synthetic intermediate allowed stepwise diarylation for the total synthesis of lamellarins G, J, L, and Z.
Scalable total synthesis of horsfiequinone A
Zhan, Rui,Du, Shou-Zhen,Kuang, Fang,Chen, Ye-Gao
supporting information, p. 1451 - 1453 (2018/03/12)
Starting from two commercially available substrates, methoxyhydroquinone and piperonyl alcohol, a scalable four-step total synthesis of horsfiequinone A was developed. The notable feature of the synthesis is the application of two continuous sequential transformations. Namely, the key aldehyde 9 and horsfiequinone A were prepared via scalable Wittig/hydrolysis and Wittig/catalytic hydrogenation/oxidation sequences, respectively. Importantly, the synthetic route required only three recrystallizations and one column chromatography purification step.
The Structure of Thalibrunine, a Reinvestigation and Revision
Wu, Jinn,Beal, Jack L.,Doskotch, Raymond W.
, p. 208 - 212 (2007/10/02)
Evidence is presented that thalibrunine has structure 2 and is the 2'-hydroxy derivative of hernandezine.Ceric ammonium nitrate oxidation of thalibrunine acetate (3) gave 2-methoxy-4-acetoxy-4',5-diformyldiphenyl ether (6), which was also prepared synthet
