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DOI: 10.1055/s-2004-831314
Synthesis of the Bicyclic [7.3.0] Enediyne System of the Maduropeptin Chromophore: Remarkable Atropisomerism of Ansamacrolactam and Isomerization of the C4-C13 Double Bond
Publication History
Publication Date:
31 August 2004 (online)
Abstract
A nine-membered diyne system of the maduropeptin chromophore was constructed for the first time using Nozaki-Hiyama-Kishi reaction. Unexpected atropisomerism of deoxyansamacrolactam and cis/trans isomerization of the exo-double bond of the chromophore were observed.
Key words
maduropeptin - chromophore - atropisomerism - enediyne - macrolactam
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References
Phenol 3 was prepared from TBS ether2g of chloroisovanilin through standard procedure in 87% overall yield: Ph3PCHCO2Me, toluene, reflux, 2 h; H2, Pd/C, EtOAc, 10 h; TBAF, THF, 30 min.
10NMR data for 6: 1H NMR (500 MHz, CDCl3): δ = 1.44 (s, 3 H), 1.52 (s, 3 H), 2.28 (br s, 1 H), 2.41 (d, 1 H, J = 2.4 Hz), 2.58 (br s, 1 H), 2.63 (dd, 1 H, J = 19.6, 3.0 Hz), 2.76 (ddd, 1 H, J = 19.6, 5.3, 2.4 Hz), 2.91 (br s, 1 H), 3.29 (br s, 1 H), 3.67-3.85 (m, 8 H), 3.94 (d, 1 H, J = 12.4 Hz), 3.96 (d, 1 H, J = 12.4 Hz), 4.39 (d, 1 H, J = 11.1 Hz), 4.42 (d, 1 H, J = 11.1 Hz), 4.77 (d, 1 H, J = 5.3 Hz), 5.19 (br s, 1 H), 5.48 (br t, 1 H, J = 6.0 Hz), 5.55 (br s, 1 H), 6.04 (br s, 1 H), 6.77 (d, 1 H, J = 8.0 Hz), 6.84 (d, 2 H, J = 8.4 Hz), 6.93 (d, 1 H, J = 8.0 Hz), 7.23 (d, 2 H, J = 8.4 Hz). 13C NMR (125 MHz, CDCl3): δ = 27.33, 27.95, 28.88, 36.48, 38.06, 38.62, 55.10, 56.01, 65.85, 71.36, 73.59, 75.15, 79.22, 80.62, 85.65, 93.40, 97.18, 111.29, 112.61, 113.56, 121.67, 124.97, 128.15, 128.37, 129.36, 129.85, 131.34, 134.55, 139.74, 142.18, 151.80, 159.04, 171.19.
11Crystal data for 7: C34H31O7NClBr·C4H8O2, M = 769.08, monoclinic, space group P2 1 /c(#14), D c = 1.481 g/cm3, Z = 4, a = 19.180 (7) Å, b = 7.690 (2) Å, c = 23.430 (3) Å, β = 93.330 (8)°, V = 3450 (4) Å3, F(000) = 1592.00, µ(MoKα) = 13.31 cm-1, R = 0.050, R w = 0.056.
18NMR and MS data for 10: 1H NMR (500 MHz, CDCl3): δ = 1.45 (s, 3 H), 1.49 (s, 3 H), 2.56 (m, 1 H, H-8′), 2.71 (ddd, 1 H, J = 19.3, 2.6, 1.3 Hz, H-11), 2.91-3.07 (m, 4 H, 2 × H-7′, H-8′, H-11), 3.42 (dtd, 1 H, J = 14.6, 7.2, 1.6 Hz, H-14), 3.82 (s, 3 H, C3′-OMe), 4.00 (dt, 1 H, J = 14.6, 7.2 Hz, H-14), 5.01 (br s, 1 H, H-5), 5.11 (br dd, 1 H, J = 6.6, 1.3 Hz, H-10), 5.25 (s, 1 H, H-8), 6.16 (t, 1 H, J = 2.6 Hz, H-12), 6.25 (td, 1 H, J = 7.2, 2.1 Hz, H-13), 6.40 (br t, 1 H, J = 7.2 Hz, NH), 6.66 (d, 1 H, J = 8.3 Hz, H-4′), 6.91 (d, 1 H, J = 8.3 Hz, H-5′). 13C NMR (125 MHz, CDCl3): δ = 27.64 (acetonide Me), 27.90 (acetonide Me), 29.00 (C7′), 34.61 (C8′), 37.18 (C14), 39.43 (C11), 55.61 (OMe), 66.07 (C5), 76.84 (C8), 81.71 (C10), 89.23 (C6), 93.96 (C7), 94.90 (C3), 95.87 (C2), 101.35 (C9), 109.21 (C4′), 112.06 (acetonide C), 125.90 (C5′), 125.96 (C1), 127.01 (C1′), 128.93 (C-13), 129.24 (C6′), 131.42 (C-4), 138.75 (C12), 141.22 (C2′), 152.13 (C3′), 171.27 (C9′). ESI-TOFMS (positive-ion): calcd for C27H26ClNO6H [M + H]+: 496.1527; found: 496.15; calcd for C27H26ClNO6NH4 [M + NH4]+: 513.1792; found 513.17.