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Volumn , Issue 3, 2007, Pages 475-479

Total synthesis and stereochemical confirmation of 2,5-diaryl-3,4- dimethyltetrahydrofuran lignans: (+)-Fragransin A2, (+)-galbelgin, (+)-talaumidin, (-)-saucernetin and (-)-verrucosin

(2) Hanessian, Stephen a Reddy, Gone Jayapal a

a UNIVERSITÉ DE MONTRÉAL (Canada)

Author keywords

Cycloetherification; Enantioselective synthesis; Lignans; Quinonoid intermediate; Tetrahydrofurans

Indexed keywords

2,5 DIARYL 3,4 DIMETHYLTETRAHYDROFURAN LIGNAN DERIVATIVE; BENZILIC ACID; FRAGRANSIN A2; GALBELGIN; LIGNAN DERIVATIVE; MESYLIC ACID DERIVATIVE; QUINONE DERIVATIVE; SAUCERNETIN; TALAUMIDIN; UNCLASSIFIED DRUG; VERRUCOSIN;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33847402645 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968019 Document Type: Article

Times cited : (25)

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31
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- Data of, )-Fragransin A2 (1, Mp 198-200°C (Lit.3a 200-202°C, α]D +77.7 (c 1.0, CHCl3, Lit.3a +79.0 (c 0.84, CHCl3, IR (thin film, 3428, 2957, 2926, 1515, 1272, 1034 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.85-6.98 (m, 6 H, 5.58 (s, 2 H, 4.65 (d, 2 H, J, 9.2 Hz, 3.94 (s, 6 H, 1.76-1.82 (m, 2 H, 1.06 (d, 6 H, J, 6.0 Hz) ppm. 13C NMR 400 MHz, CDCl 3, δ, 146.2, 144.7, 134.0, 119.0, 113.6, 108.0, 88.0, 55.6, 50.6, 13.47 ppm. HRMS: m/z calcd for C20H25O 5 [M, H, 345.1698; found: 345.1696
- +: 345.1698; found: 345.1696.

32
- 33847354696
- Dataof(, Galbelgin(2, Mp 140-142°C (Lit.4c 141-142°C, α]D +83.4 (c 0.47, CHCl3, Lit.4c -85.1 (c 0.047, CHCl3) for, )-galbelgin, IR (thin film, 2957, 2929, 1515, 1263, 1028 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.84-7.01 (m, 6 H, 4.68 (d, 2 H, J, 9.2 Hz, 3.93 (s, 6 H, 3.90 (s, 6 H, 1.78-1.87 (m, 2 H, 1.07 (d, 6 H, J, 5.6 Hz) ppm. 13C NMR 400 MHz, CDCl3, δ, 148.6, 148.0, 134.5, 118.2, 110.4, 108.7, 88.0, 55.54, 55.52, 50.6, 13.5 ppm. HRMS: m/z calcd for C22H29O5 [M, H, 373.2009; found: 373.2014
- +: 373.2009; found: 373.2014.

33
- 33847403955
- Data of, )-Talaumidin (3, Colorless oil; [α]D +76.0 (c 0.5, CHCl3, Lit.9 -81.8 (c 0.43, CHCl3) for, )-talaumidin, 1H NMR (400 MHz, CDCl 3, δ, 6.77-6.97 (m, 6 H, 5.96 (s, 2 H, 5.57 (br s, 1 H, 4.63 (d, 2 H, J, 8.8 Hz, 3.93 (s, 6 H, 1.74-1.82 (m, 2 H, 1.05 (d, 3 H, J, 5.6 Hz, 1.04 (d, 3 H, J, 6.0 Hz) ppm. 13C NMR 400 MHz, CDCl3, δ, 147.4, 146.6, 146.2, 144.7, 136.2, 133.7, 119.3, 119.0, 113.6, 108.1, 107.6, 106.2, 100.6, 88.1, 87.8, 55.6, 50.8, 50.5, 13.45, 13.43 ppm. HRMS: m/z calcd for C20H23O 5 [M, H, 343.1540; found. 343.1553
- +: 343.1540; found. 343.1553.

34
- 84958315401
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35
- 33847388404
- 21, Data of, )-Verrucosin (4, Colorless oil; [α] D -16.14 (c 0.96, CHCl3, Lit.3a +14.8 (c 1.38, CHCl3) for, )-verrucosin, IR (thin film, 3435, 2937, 2963, 1510, 1266, 1033 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.81-7.07 (m, 6 H, 5.62 (s, 1 H, 5.56 (s, 1 H, 5.14 (d, 1 H, J, 8.6 Hz, 4.42 (d, 1 H, J, 9.3 Hz, 3.94 (s, 3 H, 3.88 (s, 3 H, 2.19-2.31 (m, 1 H, 1.76-1.86 (m, 1 H, 1.08 (d, 3 H, J, 6.5 Hz, 0.68 (d, 3 H, J, 7.0 Hz) ppm. 13C NMR100 MHz, CDCl3, δ, 146.1, 145.8, 144.8, 144.2, 132.9, 132.4, 119.5, 118.9, 113.8, 113.5, 109.4, 109.3, 87.0, 82.8, 55.50, 55.46, 47.3, 45.6, 14.6, 14.5 ppm. HRMS: m/z calcd for C20H25O 5 [M, H, 345.1698; found: 345.1693
- +: 345.1698; found: 345.1693.

36
- 33847403478
- Data of, )-Saucernetin (5, Mp 77-79°C (Lit.6c 78-80°C, α]D -44.2 (c 0.5, CHCl3, lit.6c +48.1 (c 0.5, CHCl3, IR (thin film, 2957, 2926, 1515, 1272, 1033 cm-1. 1H NMR (400 MHz, CDCl3, δ, 6.85-6.90 (m, 6 H, 5.47 (d, 2 H, J, 6.0 Hz, 3.92 (s, 6 H, 3.90 (s, 6 H, 2.25-2.32 (m, 2 H, 0.71 (d, 6 H, J, 6.4 Hz, 13C NMR 400 MHz, CDCl3, δ, 148.2, 147.5, 133.6, 118.0, 110.3, 109.1, 83.1, 55.5, 43.7, 14.4 ppm. HRMS: m/z calcd for C22H29O5 [M, H, 373.2009; found: 373.2014
- +: 373.2009; found: 373.2014.

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