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Volumn , Issue 15, 2007, Pages 2359-2362

Synthesis of the FG fragment of the pectenotoxins

Author keywords

Cyclization; Epoxidation; Pectenotoxins; Shellfish toxins; Wittig reaction

Indexed keywords

ALKENE; PATINOPECTEN YESSOENSIS EXTRACT; PECTENOTOXIN; PECTENOTOXIN 4; PECTENOTOXIN 7; PECTENOTOXIN 8; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 34948850747     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985600     Document Type: Article
Times cited : (25)

References (39)
  • 31
    • 34948847298 scopus 로고    scopus 로고
    • Selected Spectral Data Compound 18: [α]D +7.2 (c 7.20, CHCl3, HRMS: m/z calcd for C 37H57O6Si: 625.3924; found: 625.3919 [M-H, IR: νmax, 3433, 2929, 2856, 1613, 1514, 1463, 1249, 1083, 835, 775 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.01 (3 H, s, Me2t-BuSi, 0.03 (3 H, s, Me 2t-BuSi, 0.85-0.94 (18 H, m, Me2t-BuSi, CH3, H-2″, 1.25-1.30(1 H, m, H-2, 1.61-1.71 (5 H, m, H-1″, H-3, 1.82-1.94 (1 H, m, H-2, 2.10-2.30 (2 H, m, H-7, 345-3.50 (3 H, m, H-1, H-8, 3.60-3.67 (1 H, m, H-5′, 3.80 (3 H, s, OMe, 3.94-4.00 (1 H, m, H-5′, 4.17-4.20 (2 H, m, H-4, H-4′, 4.49-4.71 (4 H, m, CH2Ar, 5.40-5.54 (2 H, m, H-5, H-6, 6.86-6.89 (2 H, m, ArH, 7.26-7.35 (7 H, m, ArH, 13C NMR (75 MHz, CDCl3, δ, 4.8 CH
    • 2Ph], 73(16).
  • 34
    • 34948845299 scopus 로고    scopus 로고
    • Selected Spectral Data Compound 20: [α]D-6.9 (c 1.75, CHCl3, HRMS: m/z calcd for C 42H55O7Si: 699.3717; found: 699.3721 [MH, IR: νmax, 3469, 3069, 2930, 2856, 1612, 1513, 1247, 1110 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.99 (3 H, d, J, 6.85 Hz, CH3, 1.08 (9 H, s, Ph2t-BuSi, 141-1.61 (2 H, m, H-4, 1.65-1.69 (2 H, dd, J, 11.5, 4.0 Hz, H-3′, 1.50-1.72 (1 H, m, H-3, 2.20-2.27 (1 H, br, C-1″-OH, 2.66 (1 H, d, J, 8.0 Hz, C-1-OH, 3.15-3.34 (2 H, m, H-5, 3.34-3.42 (1 H, m, H-1, 3.56-3.72 (3 H, m, H-1″, H-2, 3.80 (3 H, s, OMe, 3.88 (1 H, m, H-5′, 4.06-4.10 (2 H, m, H-4′, H-2′) 4.22 (1 H, d, J, 11.5 Hz, CH2Ar, 4.35-441 (2 H, m, CH 2Ar, 4.44 (1 H, d, J, 11.5 Hz, CH2Ar, 6.85-6.88 2 H, m, ArH, 7.16-7
    • +], 199 (10), 197 (8), 137 (14), 136 (13), 135 (9), 122 (10), 121 (100), 91 (27).
  • 38
    • 34948855622 scopus 로고    scopus 로고
    • Selected Spectral Data Compound 2: [α]D-6.0 (c 0.2, CHCl3, HRMS: m/z calcd for C 41H55O8Si: 703.3666; found: 703.3670 [M-H, IR: νmax, 2932, 1729, 1613, 1514, 1428, 1248, 1170, 1093, 821, 703 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.03-1.16 (20 H, m, Ph2t-BuSi, H-3′, 1.21 (3 H, d, J, 7.2 Hz, C-4-CH3, 1.34-1.40 (1 H, m, H-5, 1.64-1.76 (1 H, m, H-5, 1.99-2.09 (1 H, m, H-4, 3.39 (3 H, s, C-2-OMe, 342-347 (2 H, m, H-6, 3.61 (1 H, d, J, 5.0 Hz, H-3, 3.73-3.77 (1 H, m, H-4′, 3.80 (3 H, OMe, OPMB, 3.93-3.98 (1 H, m, H-5′, 4.03-4.07 (1 H, m, CH2, OPMB, 4.10-4.21 (2 H, m, H-1″, 4.23-4.27 (1 H, m, CH2, OPMB, 4.41 (1 H, t, J, 7.5 Hz, H-2′, 6.82-6.86 (2 H, m, ArH, 7.09-7.12 (2 H, m, ArH, 7.30-7.42 (6 H, m, ArH, 7.65-7.76 4 H, m, ArH
    • +, 673 (2), 647 (0.2), 617 (2), 597 (2), 383 (18), 239 (7), 197 (7), 121 (100), 89 (18).
  • 39
    • 34948879868 scopus 로고    scopus 로고
    • The stereochemistry at C2 in 2 was assumed to be that in which the OMe group adopts an axial position due to stabilization by the anomeric effect.
    • The stereochemistry at C2 in 2 was assumed to be that in which the OMe group adopts an axial position due to stabilization by the anomeric effect.


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