Compound 21
(5R,6S)-2,5,6-trimethyl-6-((phenylthio)methyl)cyclohex-2-en-1-one
From: Isolation, synthesis and bioactivity studies of phomactin terpenoids
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Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
A 500 mL Schlenk flask was charged with cyclobutanol 20 (see Supplementary information) (7.50 g, 28.8 mmol), [Rh(cod)OH]2 (1.00 g, 2.19 mmol) and MeOH (150 mL) in a nitrogen-filled glovebox. The vessel was tightly sealed, removed from the glovebox, and heated to 60 °C and held at this temperature. After 60 h, the reaction mixture was allowed to cool to room temperature and filtered through a pad of Celite®. The resulting filtrate was then concentrated and purified by column chromatography (SiO2, 5% to 10% EtOAc/ hexane) to give cyclohexenone 21 (5.60 g, 75%) as a yellow oil. Rf: 0.75 (25% EtOAc/ hexanes); Optical Rotation: [α]22D = −48 (c 0.46, CHCl3); 1H NMR (600 MHz, CDCl3): δ 7.42 (dt, J = 7.4, 1.3 Hz, 2H), 7.27 (tt, J = 7.4, 1.3 Hz, 2H), 7.18 (tt, J = 7.4, 1.3 Hz, 1H), 6.63 (ddq, J = 5.7, 2.8, 1.4 Hz, 1H), 3.61 (d, J = 12.2 Hz, 1H), 2.93 (d, J = 12.2 Hz, 1H), 2.57–2.51 (m, 1H), 2.36–2.30 (m, 1H), 2.13 (ddq, J = 19.2, 9.9, 2.5 Hz, 1H), 1.77 (dt, J = 2.7, 1.5 Hz, 1H), 1.03 (s, 3H), 0.91 (d, J = 6.9 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 202.3, 143.2, 137.7, 134.2, 130.4, 128.9, 126.3, 50.1, 40.6, 34.1, 31.4, 17.8, 16.6, 15.4; HRMS (EI): Calc’d for C16H20OS [M]+: 260.1235, found: 260.1233.
