Registro:

Referencias:

• Fenical, Sims, Cyclic polysulfides from the red alga Chondria californica (1976) The Journal of Organic Chemistry, 41, pp. 2465-2467
• Fenical, Sims, (1974) Tetrahedron Lett., 15, pp. 1137-1140
• Oztunc, Imre, Lotter, Wagner, Ent-13-epiconcinndiol from the red alga Chondria tenuissima and its absolute configuration (1989) Phytochemistry, 29, pp. 3403-3404
• Fattorusso, Piattelli, Amino Acids from Marine Algae (1980) Marine Natural Products, Chemical and Biological Perspectives, pp. 95-140. , P.J. Scheuer, Academic Press, Inc, New York
• Maeda, Kodama, Tanaka, Yoshizumi, Takemoto, Nomoto, Fujita, Structures of isodomoic acids A, B and C, novel insecticidal amino acids from the red alga Chondria armata. (1986) CHEMICAL & PHARMACEUTICAL BULLETIN, 34, pp. 4892-4895
• Maeda, Kodama, Tanaka, Yoshizumi, T., Nomoto, T., (1987) Tetrahedron Lett., 28, pp. 633-636
• Voucher specimens (BA 35284) are deposited at the Museo Argentino de Ciencias Naturales “Bernardino Rivadavia”, Buenos Aires, Argentina; 2: oil, HRMS (FAB+): m/z 214.0732 (calcd for C12H10O2N2 214.0742); EIMS (20 eV): m/z 214 (M+), 100, 213 (2), 185 (20), 170 (14), 143 (47); UV (MeOH): λmax 218 (24010), 276 (10130), 354 (20990); IR (film): 3200, 1715, 1660, 1605, 1350, 1200, 1110, 730 cm−1; 13C NMR (75 MHz, acetone-d6) δ163.4 (H-CO), 158.1 (CO), 139.9 (C-11), 138.7 (C-8), 133.2 (C-8), 126.0 (C-9), 123.7 (C-6), 122.0 (C-5), 121.1 (C-4), 113.7 (C-3), 113.6 (C-10), 113.2 (C-7); 1H NMR (300 MHz, acetone-d6): δ10.97 (bs, H-1), 10.10 (bs, OC-NH*-CO), 9.19 (d, J= 9.6,H-CO), 8.07 (d, J=15.6 H-11), 7.99 (dd, J= 7; 1.5, H-4), 7.91 (s, H-2), 7.53 (dd, J=7; 1.5, H-7), 7.23 (m, 2H, H-5,6), 6.84 (d, J=15.6, H-10); No good mass spectra could be obtained by EI at 70 eV probably due to the formation of dimers; 3: yellow crystals (MeOH/H2O), mp: 193 − 194 C; HRMS (FAB+): m/z 328.1450 (M+1)+ (calcd for C21H18ON3 328.1448) EIMS (20 eV): m/z 327 (M+, 100), 186 (22), 170 (20), 117 (16); UV (MeOH): λmax 208 (27730), 226 (31190), 278 (12920), 364 (26490); IR (film): 3300, 3200, 1630, 1410, 1260, 740 cm−1; 13C NMR (75 MHz, acetone-d6): δ164.7 (CO), 138.5 (C-9′), 135.7 (C-11), 130.8 (C-9), 130.6 (C-2), 126.2 (C-8), 123.3 (C-2′ and C-8′), 123.2 (C-5), 122.4 (C-6′), 121.3 (C-6 and C-11′), 120.8 (C-4), 120.2 (C-4′), 120.1 (C-5′), 115.8 (C-10), 113.9 (C-3), 113.6 (C-3′), 112.8 (C-7), 112.6 C-7′, 106.5 (C-10′); 1H NMR (300 MHz, acetone-d6): δ10.95 (bs, H-1), 10.40 (bs, H-1′), 9.64 [[Truncated]]; 4: yellow crystals (MeOH/H2O), mp: 208 − 209 C; HRMS (FAB+): m/z 343.1320 (calcd for C21H17O2N3 343.1321); EIMS (20 eV): m/z 343 (M+, 2), 186 (5), 158 (3), 133 (24), 117 (100); UV (MeOH): λmax 206 (26154), 222 (25134), 274 (10923), 368 (21846); IR (film): 3400, 3100, 1630, 1580, 1560, 1530, 1245, 740 cm−1; 13C NMR (75 MHz, acetone-d6): δ165.1 (CO), 144.7 (C-7), 138.2 (C-9′) 136.3 (C-11), 130.5 (C-2), 130.4 (C-9), 123.8 (C-2′), 122.5*(C-6′), 122.4 (C-5), 121.4 (C-11′), 120.3 (C-4′), 120.2 *(C-5′), 115.6 (C-10), 113.7 (C-3), 113.6 (C-3′), 112.5 (C-4; C-8), 112.4 (C-7′), 107.9 (C-6), 105.7 (C-10)* assignments may be interchanged 1H NMR, 300 MHz, [[Truncated]]; 7: 1H NMR (300 MHz, acetone-d6): δ10.67 (bs, H-1), 10.08 (bs, H-1′), 7.94 (bd, J=7.5, H-4), 7.78 (d, J=15.6, H-10), 7.69 (s, H-2), 7.60 (d, J=7.5, H-7′), 7.47 (bd, J=7.5, H-7), 7.36 (d, J=7.5, H-4′), 7.21 (bs, H-2′), 7.13 (m, 2H, H-5′,6′), 7.03 (m, 2H, H-5,6), 6.81 (d, J=15.6, H-10), 4.97 (m, H-11′), 4.12 (q, 2H, J=7, −O-CH2 *-CH3), 3.35 (m, 2H, H-10′), 1.15 (t, 3H, J=7, −CH3). 13C NMR (75 MHz, acetone-d6): δ173.2 (CO ester), 170.0 (CO amide), 134.8 (C-11), 130.9 (C-9), 129.9 (C-2), 123.9 (C-2′), 123.8 (C-8), 122.9 (C-5), 121.8 (C-6), 121.0 (C-4), 120.7 (C-4′), 119.2*(C-6′), 119.0*(C-5′), 118.8 (C-3′), 116.3 (C-10), 113.6 (C-3), 112.5 (C-7), 111.7 (C-7′), 61.1, O-CH [[Truncated]]

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