Compound 19b

(3aR,3bS,5S,6S,6aS,7S,8S,9aR,9bR,10R,11R,11aS)-7-((tert-Butyldimethylsilyl)oxy)-6,6a,11-trihydroxy-5,8,10-trimethyl-11a-(prop-1-en-2-yl)dodecahydro-3aH-5,9b-epoxyazuleno[5',4':3,4]benzo[1,2-d][1,3]dioxol-2-one

From: Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities

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InChIKey BIZYCJHVLQXMGK-FKURQODYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

See 20 for synthetic procedure. TLC: Rf = 0.24 (20% EtOAc/petroleum ether). 1H-NMR (CDCl3, 500 MHz) δ 5.22 (brd q, 1H, J = 1.5 Hz, C16-H), 4.84 (s, 1H, C16-H), 4.68 (d, 1H, J = 8.0 Hz, C14-H), 4.00 (dd, 1H, J1 = 11.5 Hz, J2 = 4.4 Hz, C12-H), 3.88 (d, 1H, J = 9.5 Hz, C3-H), 3.22 (brd d, 1H, J = 10.0 Hz, C5-H), 3.09-3.15 (2H, m, C8-H & C4-OH), 2.78 (dd, 1H, J1 = 13.0 Hz, J2 = 10.0 Hz, C7-H), 2.15-2.22 (1H, m, C2-H), 2.10 (d, 1H, J = 4.5 Hz, C12-OH), 2.07 (d, 1H, J = 10.0 Hz, C5-OH), 1.98 (s, 3H, 3 x C17-H), 1.89-1.95 (m, 2H, C7-H & C11-H), 1.75-1.84 (m, 2H, C1-H & C10-H), 1.35 (s, 3H, 3 x C20-H), 1.11 (d, 3H, J = 7.0 Hz, 3 x C18-H), 0.92-0.94 (m, 12H, 3 x C19-H & Si(CH3)2(C(CH3)3)), 0.14 (s, 3H, Si(CH3)2(C(CH3)3)), 0.10 (s, 3H, Si(CH3)2(C(CH3)3)). 13C-NMR (CDCl3, 125 MHz) δ 152.9, 140.9, 115.4, 89.9, 84.4, 82.4, 78.8, 78.1, 76.4, 71.8, 48.0, 38.7, 35.6, 34.1, 34.1, 32.1, 29.7, 25.7, 22.8, 22.0, 18.1, 17.1, 10.2, -4.6, -5.3. IR (NaCl Thin Film) ν = 3479 (brd), 2950, 2930, 2852, 1799, 1455, 1375, 1252, 1093, 1049, 981, 839, 779 cm-1. MS (TOF MS ES+) m/z Calculated for C27H44O8Si + Na (M+Na): 547.2703; Found: 547.2703. [α]D = 25.4 ° (c 0.23, CH2Cl2).

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