DOI: 10.1039/A808714H
(Paper)
Reference Section for: Chem. Commun., 1999, 117-118
The first total synthesis of (±)-pallescensin B
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Wen-Cheng Liu and Chun-Chen Liao
Abstract
The first total synthesis of the title compound has been accomplished using an intramolecular Diels–Alder reaction of a masked o-benzoquinone, anionic [1,3]-rearrangement of a vinylbicyclo[2.2.2]octenol and intramolecular hetero-Michael addition of a hydroxy enone as the key steps.
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- Selected data for synthetic 1: νmax(neat)/cm–1 2922 (s), 1505 (m), 1439 (m); δH(400MHz, CDCl3) 7.07 (d, J 1.6, 1H), 6.03 (d, J 1.6, 1H), 5.81 (dq, J 6.9, 1.2, 1H), 3.43 (ddd, J 6.9, 6.6, 2.4, 1H), 2.36–2.28 (m, 1H), 2.21–2.04 (m, 3H), 1.92–1.84 (m, 1H), 1.60–1.53 (m, 2H), 1.79 (d, J 1.2, 3H), 0.91 (s, 3H), 0.77 (s, 3H); δC(100 MHz, CDCl3) 153.2 (C), 141.2 (C), 138.0 (CH), 120.7 (CH), 118.1 (C), 113.5 (CH), 50.1 (CH), 43.8 (CH2), 36.7 (CH3), 33.8 (CH), 33.5 (C), 30.5 (CH2), 29.9 (CH3), 23.6 (CH3), 22.0 (CH2); m/z(70 eV) 216 (M+); HRMS (EI): Calc. for C15H20O: 216.1514; found: 216.1504.