D
Synlett
A. Venkanna et al.
Letter
References and Notes
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3
15 min. A solution of enone 3 (0.150 g, 4.1 mmol) in THF (8 mL)
(
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4
(
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aqueous layer was extracted with EtOAc, the combined organic
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filtered, and concentrated under reduced pressure. The residue
was purified by flash chromatography, eluting with 10%
2
4
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EtOAc/hexane to give compound 18 (0.128 g, 85%, ee 98%) as a
25
colorless liquid: [α]D –2.53 (c 4.8, CHCl ). IR (KBr): νmax= 3562,
2
3
2
972, 2920, 2847, 1586, 1448, 1227, 1107, 720 cm–1. 1H NMR
(
300 MHz, CDCl ): δ = 6.73 (s, 1 H), 6.33 (s, 1 H), 5.93–5.84 (m, 5
3
2
H), 5.77–5.70 (m, 1 H), 4.88–4.82 (m, 1 H), 3.85 (s, 3 H), 3.83 (s,
(
(
(
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3
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3
130.0, 129.2, 121.1, 119.9, 103.5, 101.1, 100.9, 98.8, 68.9, 59.4 (2
C), 31.9 ppm. HRMS: m/z calcd for C20H20O : 371.1052;
7
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371.1048 [M + H] .
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©
Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–D