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DOI: 10.1055/s-2003-36238
Synthesis of 2-Carboxy-6-hydroxyoctahydroindole (Choi) Core Unit for the Synthesis of Aeruginosins
Publication History
Publication Date:
18 December 2002 (online)
Abstract
The synthesis of N,O-protected 2-carboxy-6-hydroxyoctahydroindole (Choi) core unit for the synthesis of aeruginosins has been described.
Key words
2-carboxy-6-hydroxyoctahydroindole - choi - aeruginosin - trypsin - thrombin
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References
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10Data of the GMMX and MOPAC calculations for 10′ and 12′ are shown in Figure [3] .
11The stereochemistry at the 6-position of 13 and 14 was determined by the chemical shifts and coupling constants in the 1H NMR spectra as shown in Figure [4] .
12The spectral data for synthetic 1 are as follows. 1H NMR (500 MHz, CDCl3): δ = 1.40 and 1.46 (9 H, each s), 1.51 (1 H, br), 1.61 (1 H, br), 1.69 (1 H, br t, J = 11.5 Hz), 1.96 (2 H, br), 2.12-2.18 (2 H, m), 2.36 (1 H, br), 3.74 (3 H, s), 4.15 (1 H, br s), 4.22 (1 H, br), 4.29 (1 H, br). 13C NMR (125 MHz, CDCl3): δ = 19.46 (CH2), 26.29 and 26.60 (each CH2, due to rotamers), 28.25 and 28.42 (each CH3, due to rotamers), 31.61 and 32.44 (each CH2, due to rotamers), 33.64 and 33.78 (each CH2, due to rotamers), 35.83 and 36.42 (each CH, due to rotamers), 51.95 and 52.13 (each CH3, due to rotamers), 53.45 and 53.69 (each CH, due to rotamers), 58.87 and 59.38 (each CH, due to rotamers), 65.92 and 66.18 (each CH, due to rotamers), 79.86 (C), 153.24 (C), 174.01 and 174.11 (each C, due to rotamers). 1H NMR (500 MHz, DMSO-d 6, 80 °C): δ = 1.36 (9 H, s), 1.43 (2 H, m), 1.51 (1 H, m), 1.85 (1 H, q-like, J = 9.9 Hz), 2.01 (2 H, m), 2.11 (1 H, dt, J = 12, 7.3 Hz), 2.26 (1 H, m), 3.65 (3 H, s), 3.89 (1 H, br), 4.01 (1 H, m), 4.16 (1 H, m). 13C NMR (100 MHz, DMSO-d 6, 80 °C): δ = 19.16 (CH2), 26.39 (CH2), 27.70 (CH3), 31.42 (CH2), 33.20 (CH2), 35.30 (CH), 51.13 (CH3), 53.39 (CH), 58.54 (CH), 63.74 (CH), 78.25 (C), 161.61 (C), 172.93 (C). Lit. [3a] [b] [α]D -31.1 (c 2.4, MeOH); [α]D 26 -36.2 (c 1.25, MeOH).