Synthesis of D-Albizziine Derivatives from L-Serine

References and Notes

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• Representative data for compounds 4–10: 4: [α]D 20 - 37.33 (c 1.5, CH3OH). 1H-NMR (200 MHz, CDCl3, TMS): δ 7.32–7.2 (m, 5H, C6H5), 4.06–3.88 (m, 2H, CH2), 3.95 (br. s. 2H, CH2), 3.8 (s, 2H, CH2), 2.91–2.8 (m, 1H, NH), 2.72–2.62 (m. 1H, CHN), 1.53 (s, 3H, (CH3)2C), 1.48 (s, 9H, (CH3)3C), 1.42 (s. 3H, (CH3)2C). 13C-NMR (50 MHz, CDCl3, TMS): δ 152.39, 151.75 (CO2), 140.42, 128.28, 127.88, 126.83 (C6H5), 93.69, 93.38 (C(CH3)2), 80.01, 79.56 (C(CH3)3), 66.29 (CH2), 57.31 (CHN), 53.84 (CH2), 51.15 (CH2), 28.35 ((CH3)3C), 27.45, 26.72 (CH3), 24.37, 23.09 (CH3). Anal. Calcd for C18H28N2O3: C, 67.47; H, 8.81; N, 8.74. Found: C, 67.48; H, 8.83; N, 8.83. 5: [α]D 20 -20.1 (c 1.5, CH3OH). 13C-NMR (50 MHz, CDCl3, TMS): δ 159.21 (NCON), 152.79 (CO2), 138.51, 128.56, 127.4, 127.19 (C6H5), 93.12 (C(CH3)2), 81.16 (C(CH3)3), 66.61 (CH2), 57.03 (CHN), 51.76 (CH2), 49.71 (CH2), 28.24 ((CH3)3C). 27.32, 23.71 (CH3). Anal. Calcd for C19H29N3O4: C, 62.79; H, 8.04; N, 11.56. Found: C, 63.04; H, 8.17; N,11.47. 6: [α]D 20 -5.9 (c 1.5, CH3OH). 1H-NMR (200 MHz, CDCl3, TMS): δ 7.38–7.22 (M, 5H, C6H5), 5.28 (d, 1H, J = 7.2, NHBoc), 4.76 (br. s, 2H, NH2), 4.56 and 4.43 (AB, 2H, J = 17.83, CH2), 3.84–3.55 (m, 4H, CH2O and CH2N), 3.22 (d, 1H, J = 9.61, CHN), 1.42 (s. 9H, (CH3)3C). 13C-NMR (50 MHz, CDCl3, TMS): δ 161.1 (NCON), 156.93 (CO2), 138.85, 129.5, 129.32, 128.14, 127.93 (C6H5), 79,53 (C(CH3)3), 61.78 (CH2), 52.26 (CH2), 51.57 (CHN), 47.52 (CH2), 28.52 ((CH3)3C). 7: [α]D 20 -13.4 (c 1.5, CH3OH). 1H-NMR (200 MHz, CDCl3, TMS): δ 8.22 (br. s, 1H, NH), 7.39–7.27 (m, 5H, C6H5), 5.32 (d, 1H, J = 4.12, NHBoc), 4.93 (d, 1H, J = 16.45, CH2Ph), 4.5–4.36 (m. 1H, CH2), 4.33 (d, 1H, J = 16.46, CH2Ph), 3.73 (m, 1H, CH2), 3.16 (t, 1H, J = 12, CHN), 1.42 (s. 9H, (CH3)3C). Anal. Calcd for C16H21N3O4: C, 60.18; H, 6.63; N, 13.16. Found: C, 60.17; H, 6.71; N, 12.96. 8: 1H-NMR (200 MHz, (CD3)2CO, TMS): δ 6.07 (m, 1H, NH), 5.85 (d, 1H, J = 9.44, NHBoc), 5.4 (br. s, 2H, NH2), 4.49 (t, 1H, J = 6.41, OH), 3.61–3.48 (m, 2H, CH2), 3.42 (m, 1H, CHN), 3.25 (dd, 2H, J = 5.49 and 5.8, CH2), 1.39 (s, 9H, (CH3)3C). 13C-NMR (50 MHz, (CD3)2CO, TMS): δ 160.99 (NCON), 156.38 (CO2), 79,7 (C(CH3)3), 61.36 (CH2), 52.49 (CHN), 40.4 (CH2), 28.38 ((CH3)3C). 9: [α]D 20 + 10.5 (c 2.3, CH3OH). 1H-NMR (200 MHz, (CD3)2CO, TMS): δ 6.49 (d, 1H, J = 6.4, NH), 6.12 (m, 1H, NH), 5.51 (br. s, 2H, NH2), 4.17 (m, 1H, CHN), 3.64–3.34 (m, 2H, CH2), 1.4 (s, 9H, (CH3)3C). 13C-NMR (50 MHz, (CD3)2CO, TMS): δ 173.00 (NCON), 160.85 (CO2H), 79.23 (C(CH3)3), 56.28 (CHN), 42.14 (CH2), 28.47 (CH3). Anal. Calcd for C9H17N3O5: C, 43.72; H, 6.93; N, 17.00. Found: C, 43.81; H, 7.10; N, 16.85. 10: [α]D 20 +12 (c 2, CH3OH). 1H-NMR (200 MHz, (CD3)2CO, TMS): δ 7.15 (m, 1H, NH), 6.60 (m, 2H, NH2), 6.17 (m, 1H, NH), 5.41 (br.s, 2H, NH2), 4.14 (m, 1H, CH), 3.45 (m, 2H, CH2), 1.40 (s, 9H, (CH3)3C). Anal. Calcd for C9H18N4O4: C, 43.90; H, 7.37; N, 22.75. Found: C, 44.05; H, 7.50; N,22.45.
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