Compound 17
(4R,5S)-4,5-dimethyl-6-methylene-5-((phenylsulfonyl)methyl)cyclohex-1-ene-1-carbaldehyde
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.
To a 250 mL round-bottomed flask containing a solution of diene S3 (see Supplementary information) (3.16 g, 10.9 mmol) in dioxane (80 mL) was added SeO2 (6.04 g, 54.4 mmol). The resulting suspension was heated to 80 °C and held at this temperature. After 5 h, the vessel 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 30% EtOAc/ hexane) to afford aldehyde 17 (1.84 g, 56%) as a pale yellow foam. Rf: 0.30 (25% EtOAc/ hexanes); Optical Rotation: [α]22D = +19 (c 0.49, CHCl3); 1H NMR (600 MHz, CDCl3): δ 9.45 (s, 1H), 7.84 (d, J = 7.7 Hz, 2H), 7.61 (t, J = 7.7 Hz, 1H), 7.54 (t, J = 7.7 Hz, 2H), 6.68 (s, 1H), 6.22 (s, 1H), 5.34 (s, 1H), 3.16 (d, J = 14.5 Hz, 1H), 3.05 (dd, J = 21.6, 6.9 Hz, 1H), 2.94 (d, J = 14.5 Hz, 1H), 2.61 (quint, J = 6.9 Hz, 1H), 2.31 (dd, J = 21.6, 6.9 Hz, 1H), 1.52 (s, 3H), 0.83 (d, J = 6.9 Hz, 3H); 13C NMR (151 MHz, CDCl3): δ 192.8, 150.9, 141.6, 140.0, 135.6, 133.7, 129.4, 127.6, 117.0, 63.8, 43.0, 33.8, 33.0, 22.4, 16.3; HRMS (ESI): Calc’d for C17H20O3NaS [M+Na]+: 327.1025, found: 327.1019.
