New Synthetic Routes to Acronycine, Noracronycine, and Their Analogues

Isolation, Characterization of Undescribed Alkaloids, and Semisynthetic Modifications of Cytotoxic Pyranoacridone Alkaloids from Glycosmis pentaphylla

“…confirmed by COSY correlations, and the position of −OH, −OCH 3 , −NCH 3 , and prenyl was confirmed by13 C HMBC and15 N HMBC corrections. The key correlations observed by 2D experiments to characterize this compound are represented in Figure…”

“…Column chromatography (SiO 2 100−200, eluted with 10% ethyl acetate) afforded the desired product as a pale-white crystalline solid (25 mg, 45% yield). mp 152−154 °C; 1 H NMR (500 MHz, CDCl 3 ): δ 8.32 (1H, d, J = 8.5 Hz), 7.63 (1H, t, J = 8.5 Hz), 7.57 (1H, d, J = 6.8 Hz), 7.27 (1H, t, J = 6.8 Hz), 7.04 (1H, t, J = 5.9 Hz), 6.74 (1H, d, J = 9.4 Hz), 6.34 (2H, s), 5.53 (1H, d, J = 9.7 Hz), 5.25 (2H, d, J = 6.2 Hz), 3.97 (3H, s), 1.53 (6H, s) 13 C NMR (125 MHz, CDCl 3 ): δ 177.9, 162. (1) or des-Nmethylacronycine (4) (0.32 mmol, 1.0 equiv) was dissolved in anhydrous DMF (3 mL) under a nitrogen atmosphere.…”

“…The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.2c08100. 1 H, 13 C NMR, and HRESIMS spectra for compounds 1−22 and 2D NMR spectra for compounds 6, 7, 10, and 11 (PDF)…”

“…13 C NMR (125 MHz) Data of Compounds 8 and 9 (CDCl 3 ) http://pubs.acs.org/journal/acsodf Article https://doi.org/10.1021/acsomega.2c08100 ACS Omega XXXX, XXX, XXX−XXX i n d i v i d u a l n o t d i r e c t l y a s s o c i a t e d w i t h s c i t e i s p r o h i b i t e d . compounds with this molecular weight in related genera across the entire Rutaceae family.…”

Studies Directed towards the Synthesis of the Acridone Family of Natural Products: Total Synthesis of Acronycines and Atalaphyllidines

“…Reisch et al synthesized noracronycine analogues by the reaction of the N -methyl-1,3-dihydroxyacridone derivative with propinols under Mitsunobu condition . Recently, Lee and co-workers reported the synthesis of acronycine and noracronycine via ethylenediamine diacetate-mediated cyclization of the dihydroxyacridone derivative followed by selective methylation . In our approach, we have successfully accomplished the synthesis of acronycine and noracronycine in a comparatively lesser number of steps with an improvement in overall yields.…”