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REVENCYT-Redidiciencia Moreno Valero José Adolfo Aislamiento, caracterización y estudio de algunas reacciones químicas de diterpenos del ent- kaurano, presentes en la Espeletia schultzii wedd parte 2 Universidad de Los Andes-Facultad de Ciencias-Postgrado en Química Aplicada. 2002. p. 68 Venezuela Disponible en: http://bdigital.ula.ve/RediCiencia/busquedas/DocumentoRedi.jsp?file=33587&type=ArchivoDocumento &view=pdf&docu=26867&col=5 ¿Cómo citar? 146 16(17) a.-EPOXI-ENT-KA.UR-9(11)-EN-19-0ATO DE METILO (14] El producto mayoritario obtenido en la reacción del éster metílico [12] con ÁciClo "mcto"-Cloropcrbenzoico, fue purific1do por cromatogwfía prcpilrativa, rindiendo un aceite iwmogéneo en capa fina. El análisis detallado de sus espectros de RMN-H1 (Fig. 14B; Tabla 14B) y de RMN-C13 (BB y DEPT) (Fig. 14C; Tabla 14C), condujeron a deducir, para este derivado, la fórmula molecular C21H300 3 • En su espectro IR (Fig. 14A; Tabla 14A), destaca una absorción i:p.tensa típica del carbonilo de un éster [vmax: 1.726 cm·1 (C=O)] y bandas atribuibles a vibraciones 1 de enlaces C-0 (vmax: 1.226 y 1.147 cm- ). Es también notable en el mismo la ausencia de absorciones características de hidroxilos, y por ello, es lógico suponer que dos de los oxígenos forman parte del éster y el tercero debe estar integrado a un grupo epóxido formado en la reacción, a expensas de uno de los dobles enlaces existentes en el éster metílico [12], utilizado como material de partida. Figura 14A: Espectro Infrarrojo (film), del 16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo (14] 80,0 70 60 so 40 %T 30 20 C·H ~~ 10 2.870 C-H C=O t.ZZ5 1.728 0,0 2.933 3700,0 3000 2000 1500 1000 450,0 cm-1 Tabla 14A: Bandas de Absorción Significativas en el Espectro IR del16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo (14] Vmax. (cm-1) 2.933 2.870 1.726 1.679 1.226 1.147 Asignación C-H C-H C=O C=C C-0 C-0 147 El espectro de RMN-H1 muestra, un triplete [8: 5,19; U= 3,5 Hz)], típico de un protón olefínico (H-11) acoplado a los hidrógenos de un metileno vecinal (H-12); en consecuencia, cabe suponer que en este derivado permanece presente el doble enlace trisustituído que poseía el compuesto de partida [12]. Esto fue también 1 cunfirmauo en el especl.ro de RMN-C \ en el cual se identificaron dos picos [8: 156,69 (C-9) y 8: 115,54 (C-11)], cuya posición y orientación en el DEPT-135, permite asignarlos a los carbonos de un doble enlace de este tipo: Más aún, el pico más apantallado, asignable a un =CH se correlaciona en el HMQC (Fig. 14F) con el triplete del protón olefínico que resuena a 8: 5,19. Al quedar confirmada la presencia en la molécula de este doble enlace, es 16 17 evidente que el otro doble enlace (el metilénico /1 ' ) fue el que se epoxidó en el transcurso de la reacción. Ello fue confirmado al observar en el espectro de RMN-H1 un par de dobletes a 8: 2,76 y 8: 2,80 U= 4,5) [H-17A y H-17B], que se correlacionan en el espectro HMQC con un pico asignable a un carbono metilénico unido a un oxígeno [8: 50,83; -CH2-0- (C-17)]; este par de dobletes se correlaciona en el espectro HMBC (Fig. 14G) con un pico (8: 69,19), propio de un carbono cuaternario unido también a un oxígeno [>C-0- (C-16)], con lo cual queda demostrada la naturaleza espiránica del grupo epóxido, y por supuesto su necesaria ubicación en C-16/C-17. Otra evidencia en favor de esta última aseveración, es la denotación de la siguiente secuencia HMBC: C-16 ~ H-14 ~ C-12/H-12 ~ C-16 ~ H-15~ C-17/H-17 ~C-13~H-14/C-14.~H-15/C-15~ H-17~C-16 ~H-13 ~C-14~ H-12~C-13~H-15. La permanencia en la molécula del grupo carbometoxi, presente en el éster de partida, fue también puesta en evidencia mediante los espectro de RMN-H1 y 13 RMN-C [.SH: 3,60, (s) (H-21); .Se: 51,28 (C-21), -OCH3 y .Se: 177,90, -0-C=O (C-19)]. Su ubicación en C-4 fue sustentada por las correlaciones en el HMBC: C-4 ~ H-5~ C-18 ~ H-3 ~ C-19 ~ H-18 ~c-5 ~ H-3~ C-4~ H-18 ~C-3 ~H-5 ~ C-19 ~H-21 Los datos analizados hasta ahora demuestran que la estructura gruesa de este derivado se corresponde con la de un 16,17-Epoxi-ent-Kaur-9(11)-en-oato de metilo. Sobre la base de su origen, hemos de aceptar que la estereoquímica en los centros quirales C-4, C-5, C-8, C-10 y C-13 es idéntica a la del éster de partida; por lo tanto sólo faltaría, para completar el estudio, determinar la estereoquímica en C-16. Ello fue posible a través del espectro NOESY (Fig. 14H), dado que en el mismo se observa que el doblete asignado a H-17A (exo) muestra NOE con la señal de H-12f3, mientras que el otro doblete, correspondiente al H-17B (endo), lo hace con la señal del H-15a. Estos hechos, unido al alto rendimiento con que se obtuvo el producto, en la reacción de epoxidación, avalan una orientación a para el anillo oxiránico. Con ello, la estructura y estereoqímicfl, del producto quedó completamente establecida, siendo éste el16,17a-Epoxi-ent-Kaur-9(11)-en-oato de metilo [14]. 148 1 Figura 14B: Espectro de R.\1N-H (CDCI3, 400 MHz), del 16(17)cx.-Epoxi-ent-Kaur-9{11)-en-19-oato de Metilo [14] H·13 H·17 1 2 1 --·--.--r-.,._.,... .... - .. .,_, ·······-·-········· ... ··- .,. .... -···~··-, ........ -,---,. ....... - ... -. ···· r··-······· ·-··· ·--······-; "'* J.t J" l'.<:: 1.! ~ ~ H-21 H-18 H-20 H-17 H-11 _J_~~- ------""' I_____..__,._,JU\..__.}!'VII\.ow./ .--,-,--.-·r-···-... --,..-.-,.-r-.--.-,--,.-.--......,...-,-, ...,-,--r-r-¡-..-..--r-r-r-,...........,.-.--,--.-....--,-.-,--,-.--.---.--,.--.--.--... PPA 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 Tabla 14B: Desplazamientos Químicos (<>) en el Espectro de RMN-H1 (CDCI3 , 400 MHz) del 16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo (14] H H-5 H-11 H-13 H-12¡3ec. H-15¡3 H-17 H-18 H-20 H-21 5 1,52 5,19 1,75 2,29 2,13 2,76 y 2,80 1,14 0,90 3,60 m d d m dt d d S S S ](Hz) =10 =3,5 - =2 y 13 =15 :::4,5 - - - 149 13 Figura 14C: Espectro de RMN-C (CDCI3 , 100 MHz), del16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo [14] 1? 11 13 1 20 1 16 17 1 14~ ··,,i 2 o 9 8 ••••• o 15 3 4 5 CJ C·18 6 J L ! c-zn 18 COOCH3 •r~t7111-.c-a~·~· ~ 19 21 C·15 1 C·Z C·6 r·•~ J 1 . C·3 C·7 ~¡ 4 ·JlWL --,---..,..·-·"-y·- :11 2:1 ao ., C-11 C·16 C-19 C-9 --~~~-~ .... ···r--·r··r --.,-·--r--.,.-,·-·-r·---r---~-,,----r--.--...---.·-r··--1·--r·--··r·-·,··--·-r--T··-r--r--,.-,,..-.--r-...---y-r- PP~ 150 140 120 tb~ 60 60 40 20 - Tabla 14C: Desplazamientos Químicos (o) en el Espectro de RMN-C 13 (CDCl3 , 100 MHz), del16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo [14] e C-1 C-2 C-3 C-4 C-5 C-6 C-7 C-8 C-9 C-10 C-11 o 40,83 20,16 38,30 44,82 46,67 18,41 29,98 42,89 156,69 38,66 115,54 Tipo >CH2 >CH2 >CH2 >C< >CH >CH2 >CH2 >C< =C< >C< =C-H Valores e C-12 C-13 C-14 C-15 C-16 C-17 C-18 C-19 C-20 C-21 deli, tomando alTMS o 32,85 40,69 43,16 49,97 69,19 50,83 28,06 177,90 23,49 51,28 como referencia interna rTipo >CH2 >CH >CH2 >CH2 0-C< O-CH2 -CH3 0-C=O -CH3 OCH3 150 1 Figura 14E: Espectro H\H -COSY (CDCI 3}, del 16(17)a-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo [14] II-1l.l H-20 H-17 J. O 1.!5 2.0 2.!5 ppm 2.5 2.0 1.5 1.0 Correlaciones Jll/H1 más Destacadas 3 151 (i) 20,16 H COOC @ 3 @ @ 28,06 51,28 177,90 Figura 14F: Espectro HMQC (CDC13), del 16(17)a.-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo [14) H-14 H-18 H-13 H-2 H-2H-7 H-1 C-6 C-2 C-20 C-18 C-12 C-3 C-13 -1 C-5 C-15 C-17 C-21 pp~ 2.5 2.0 1.5 1.0 152 Figura 14G: Espectro HMBC (CDC13), del 16(17)a-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo (14] C-20--~ Correlaciones que Determinan la Posición .. del Grupo Carbometoxi ... 2.5 1.0 Correlaciones que Determinan la Posición del Grupo Epóxido 16(17) Correlaciones que Determinan la Posición del Doble Enlace Trisustituido ~9 • 11 153 Figura 14H: Espectro NOESY (CDCI3), del 16(17)a-Epoxi-ent-Kaur-9(11)-en-19-oato de Metilo [14] 1.0 1.5 2.0 2.5 Plll Efectos NOE más Significativos IH-12aaxl" ~t)H-12f3ec 1" .
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