Synthesis of intermediate for lamellarin H

Lamellarins and Related Pyrrole-Derived Alkaloids from Marine Organisms

“…Synthesis of Lamellarins D (35), L (15), and N (40) a a Reagents and conditions: (i) 97 or 98 (1.0 equiv), Pd(PPh 3 ) 4 (2 mol %), THF, reflux, 4 h (99, 76%; 100, 77%); (ii) (1)101 (2.0 equiv), Pd(PPh 3 ) 4 (8 mol %), THF, reflux, 18 h, (2) concd HCl, MeOH, reflux 1 h (102, 98%; 103, 95%); (iii) (1) 40% KOH-EtOH (1/1), reflux, 3 h, (2) cat. p-TsOH, CH 2 Cl 2 , reflux, 1 h (104, 90%; 105, 91%); (iv) Cu 2 O, quinoline, 220 °C, 7 min (106, 94%; 107, 99%); (v) …”

“…In 2005, a new and simple route was developed to synthesize lamellarin H 37 and its derivatives. The fabricated intermediate, 2,4,5-trimethoxy-α-chloroacetophenone, was the key starting material for this synthesis . The next year the same group reported the synthesis of the second intermediate of lamellarin H 37 , 1-(3,4-dimethoxyphenyl)-8,9-dimethoxy-2-(2,4,5-trimethoxyphenyl)-pyrrolo-[2,1-α]-isoquinoline …”

“…In earlier surveys we comprehensively reviewed several intriguing groups of marine alkaloids, including the manzamine- and bromotyrosine-derived alkaloids. , The number of reported marine alkaloids continues to grow at an increasing rate, and in recent years, the lamellarins and related pyrrole-derived alkaloids (lukianols, polycitrins, polycitones, storniamides, didemnimides, ningalins, and purpurone, Table ) − have been regarded as a group of marine alkaloids with promising biological activities. As a result, these compounds have been the subject of several previous reviews regarding their chemistry and pharmacology. − In addition, the lamellarins and related pyrrole-derived alkaloids have also provoked a great deal of interest in regard to their synthesis (Table ). ,− ...…”

Los Compuestos Fenólicos, Un Acercamiento A Su Biosíntesis, Síntesis Y Actividad Biológica

“…Otros efectos del ácido chebulínico resultan ser su efecto inhibitorio sobre las células de la leucemia humana y su citotoxicidad contra células malignas como el adenocarcinoma y tumores mamarios, osteosarcoma, cáncer de próstata y adenocarcinoma de colon en humanos (Yi et al, 2006). Por otra parte, la lamellarina H también muestra algún tipo de actividad antitumoral, en particular contra el cáncer de pulmón en humanos (You, Yang, Wang, & Li, 2005). GL Hertog et al, 1995).…”

Pyrrolo[2,1-α]isoquinoline as a skeleton for the synthesis of bioactive lamellarin H

“…Using a different route, lamellarin H was synthesized by Faulkner et al [6] in 2002. Recently, we designed a new and simple route and synthesized the first intermediate, 2,4,5-trimethoxy-α-chlor-acetophenone, for lamellarin H [7]. The synthesis of the second intermediate of lamellarin H, 1-(3,4-dimethoxy-phenyl)-8,9-dimethoxy-2-(2,4,5-trimethoxy-phenyl)-pyrrolo-[2,1-α]-isoquinoline (intermediate 2), has not been reported in detail up to now.…”