2151-16-8Relevant academic research and scientific papers
Synthetic studies on Sch 202596, an antagonist of the galanin receptor subtype GalR1: An efficient synthesis of (±)-geodin, the spirocoumaranone part of Sch 202596
Katoh, Tadashi,Ohmori, Osamu,Iwasaki, Katsuhiko,Inoue, Munenori
, p. 1289 - 1299 (2007/10/03)
An efficient and facile synthesis of (±)-geodin [(±)-2] corresponding to the spirocoumaranone part of Sch 202596 (1) was accomplished in a convergent manner. The synthetic method features (i) a coupling reaction of the aryl aldehyde 6 with the aryl lithium 7 generated in situ from the aryl bromide 8 to deliver the highly substituted diaryl methanol 24 (6+7→24) and ii) oxidative spirocyclization reaction of the benzophenone 4 to construct the requisite spirocoumaranone skeleton [4→(±)-2] as the key steps. The aromatic segments 6 and 8 were prepared from commercially available methyl 3,5-dihydroxybenzoate (9) and 5-methylresorcinol (10), respectively.
Studies toward the total synthesis of Sch 202596, an antagonist of the galanin receptor subtype GalR1: Synthesis of geodin, the spirocoumaranone subunit of Sch 202596
Katoh, Tadashi,Ohmori, Osamu
, p. 465 - 469 (2007/10/03)
An efficient synthesis of (±)-geodin [(±)-2] corresponding to the spirocoumaranone subunit of Sch 202596 (1) was accomplished in a convergent manner by utilizing coupling reaction of the aryl aldehyde 5 with the aryl bromide 6 and oxidative spirocyclization of the benzophenone 4 as the key steps. The aromatic segments 5 and 6 were prepared from commercially available methyl 3,5-dihydroxybenzoate (7) and 5-methylresorcinol (8), respectively.
