Compound G10

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InChIKey IFYWTLQMNWNCFH-DHXZDTOLSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound G10 was prepared according to the procedure of Cross, B. E. (Cross, B. E. Gibberellic Acid. Part 1. J. Chem. Soc., 4670-4676, (1954).) Gibberellic acid (1.404 g, 4.05 mmol) was dissolved in hydrochloric acid (1.2 M, 20 mL) in a round bottom flask and heated for 2.75 hours at 65 °C. The reaction was cooled, and the solid precipitate was filtered and washed with water. G10, a known compound, was isolated as a white solid (863 mg, 75% yield). ¹H NMR (d₆-acetone, 500 MHz): δ 10.97 (br s, 1H), 7.10 (t, J = 7.5 Hz, 1H), 6.98 (d, J = 7.6 Hz, 1H), 6.95 (d, J = 7.4 Hz, 1H), 4.99 (dt, J = 2.7, 1.4 Hz, 1H), 4.70 (t, J = 2.0 Hz, 1H), 3.98 (s, 1H), 2.88 (dd, J = 12.6, 5.0 Hz, 1H), 2.31 - 2.21 (m, 3H), 2.20 (s, 3H), 2.08 - 1.99 (m, 2H), 1.93 (td, J = 12.2, 5.1 Hz, 1H), 1.89 (dd, J = 10.3, 2.6 Hz, 1H), 1.71 - 1.62 (m, 1H), 1.54 (qd, J = 12.7, 5.1 Hz, 1H). ¹³C NMR (d₆-acetone, 125 MHz): δ 172.7, 155.9, 145.7, 139.7, 135.8, 129.3, 127.9, 120.3, 103.1, 80.6, 55.2, 53.8, 52.7, 49.1, 40.7, 34.9, 22.8, 20.0. HRMS(ESI): m/z calc. for C₁₈H₂₁O₃ [M+H]⁺: 285.1491, found: 285.1491. HRMS(ESI): m/z calc. for C₁₈H₂₀O₃Na [M+Na]⁺: 307.1310, found: 307.1307.