Sterols in marine invertebrates. 49. Isolation and structure elucidation of eight new polyhydroxylated sterols from the soft coral Sinularia dissecta

Abstract

1316 cm-'; MS, mle (relative intensity) 217 (M', 4), 175 (13), 174 (loo), 162 (16), 159 (28), 56 (15), 43 (36). Anal. Calcd for Cl3HI5NO2: C, 71.86; H, 6.86; N, 6.45. Found: C, 72.10; H, 6.98; N, 6.49. The ketone 32 was reduced in a similar way as that of 7a to give 33 (85%). 6,7-Dihydro-5hydroxy1,6,6-trimethyl-3,4-benzazepin-2(5H)-one (33): mp 188-189 C (from ethanol); 'H NMR (CDC13) b 1.14 (s,3 H, MeCMe), 2.10 (s,3 H, MeCMe), 2.62 and 2.90 (ABq, J = 14 Hz, 2 H,NCH,),3.08 (9, 3 H,NMe),3.57 (8, 1 H,HCOH), 4.20 (s, 1 H, OH), 7.2-7.8 (m, 4 H, Ar H); IR (KBr) 3305 (OH), 1625 (amide), 1595, 1428, 1256, 1058 cm-l; MS, mle relative intensity) 219 (M', 100), 190 (61), 161 (56), 44 (100). Anal. Calcd for C13H1,N02: C, 71.20; H, 7.82; N, 6.39. Found C, 71.20; H,