Delta-Valerolactone → HCID 19010457、化合物

反応式

Br[C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]([CH2:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:5](=[O:26])[C:4]=2[CH:3]=1.[Li]CCCC.[C:32]1(=[O:38])[O:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C1COCC1>[OH:38][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([C:2]1[S:10][C:9]2[CH2:8][CH2:7][N:6]([CH2:11][CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:5](=[O:26])[C:4]=2[CH:3]=1)=[O:37]

参加物

実験手順

A solution of 3-1 (0.66 g, 1.5 mmoles) in THF (30 ml) was cooled to -78° and treated with n-BuLi (3.0 mmoles) and the resulting yellow brown solution was stirred for 30 minutes. Then, valerolactone (0.16 g, 1.65 mmoles) was added and this was stirred at -70° for 6 hours and then overnight at ambient temperature. The reaction mixture was cooled to -10°, quenched with 10% KHSO4 and concentrated. The residue was taken up in H2O/EtOAc and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with hexane (3)/acetone(2) to give 4-1, Rf 0.35.