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Volumn , Issue 2, 2007, Pages 219-222

A new, highly stereoselective synthesis of β-unsubstituted (Z)-γ-alkylidene-butenolides using bromine as a removable stereocontrol element

(6) Boukouvalas, John a Beltrán, Paola P a Lachance, Nicolas a Côté, Sébastien a Maltais, François a Pouliot, Martin a

a UNIVERSITÉ LAVAL (Canada)

Author keywords

2 silyloxyfurans; Aldol reaction; Bromobutenolides; Dehalogenation; Stereoselectivity

Indexed keywords

AGENTS AFFECTING LIPID METABOLISM; ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; BETA GAMMA ALKYLIDENEBUTENOLIDE DERIVATIVE; BROMINE; BUTENOLIDE; CHAMAEMELUM NOBILE EXTRACT; EREMOLACTONE; LACTONE DERIVATIVE; MELODORINOL; PLANT EXTRACT; THIOPHENELACTONE DERIVATIVE; UNCLASSIFIED DRUG; XERULIN;

ALDOL REACTION; ARTICLE; CHAMAEMELUM; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 33847060907 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968004 Document Type: Article

Times cited : (50)

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- Typical Procedure: To a solution of 813 (147 mg, 0.903 mmol) in anhyd CH2Cl2 (3 mL) at 0°C were successively added TBSOTf (207 μL, 0.903 mmol) and Et3N (125 μL, 0.903 mmol, The mixture was stirred for 30 min at 0°C, then cooled to -78°C, and then p-anisaldehyde (100 μL, 0.821 mmol) was added. After stirring at -78°C for 1 h, DBU (251 μL, 1.64 mmol) was added and the resulting dark purple solution was allowed to warm to r.t. and stirred for an additional 1.5 h before quenching with 15% aq tartaric acid. The aqueous phase was extracted with CH2Cl2 (3 x) and the combined organic layers were washed with sat. aq NaHCO3, dried over MgSO 4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; EtOAc-CH2Cl 2-hexanes, 1:3:10) to afford 6b 196 mg, 85, as a pale red-brown soli
- 7a

44
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48
- 33847071619
- Silyloxyfuran 9 was prepared in 98% yield by silylation (TBSOTf, Et3N, CH2Cl2, r.t, of the readily available β-bromo-α-methylbutenolide: Svendsen, J. S, Sydnes, L. K. Acta Chem. Scand. 1990, 44, 202. Data for 9: colorless oil. 1H NMR (300 MHz, CDCl3, δ, 0.22 (s, 6 H, 0.97 (s, 9 H, 1.80 (s, 3 H, 6.86 (s, 1 H), 13C NMR (75 MHz, CDCl 3, δ, 4.5, 7.4, 17.9, 25.4, 94.0, 104.3, 129.2, 152.4. HRMS EI, m/z calcd for C11H19BrO2Si: 290.0338; found: 290.0331
- 2Si: 290.0338; found: 290.0331.

49
- 33847040367
- Data for 11a: orange oil. 1H NMR (400 MHz, CDCl 3, δ, 0.93 (t, J, 7.3 Hz, 3 H, 1.37 (m, 2 H, 1.49 (m, 2 H, 2.41 (q, J, 7.6 Hz, 2 H, 5.62 (dt, J, 0.5, 8.0 Hz, 1 H, 6.34 (d, J, 0.5 Hz, 1 H, 13C NMR (75 MHz, CDCl 3, δ, 13.7, 22.3, 26.1, 30.8, 117.3, 119.6, 136.9, 148.1, 167.0. HRMS (EI, m/z calcd for C9H11BrO 2: 229.9942; found: 229.9938. Data for 11b: orange oil. 1H NMR (300 MHz, CDCl3, δ, 0.90 (t, J, 7.l Hz, 3 H, 1.31-1.50 (m, 4 H, 1.96 (s, 3 H, 2.37 (q, J, 7.4 Hz, 2 H, 5.47 (t, J, 7.9 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 10.2, 13.7, 22.3, 25.8, 31.0, 114.5, 128.1, 132.2, 147.0, 167.9. HRMS (EI, m/z calcd for C10H13BrO2: 244.099; found: 244.0098. Data for 11c: yellow oil. 1H NMR 300 MHz, CDC
- 4: 274.9919; found: 274.9915.

50
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