Compound G11

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InChIKey ASZCVNVMQXNJGH-LGRHPFTQSA-N

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

Compound G11 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 (959 mg, 2.77 mmol) was suspended in aqueous hydrochloric acid (2.4 M, 150 mL) in a round bottom flask and refluxed for 2 hours. The solid crust that formed during the course of the reaction was periodically broken up with a glass rod. After refluxing, the reaction was filtered hot, and the solid was washed with water to provide known compound G11 as a white solid (298 mg, 38% yield). ¹H NMR (CDCl₃, 500 MHz): δ 7.22 (t, J = 7.5 Hz, 1H), 7.07 (d, J = 7.6 Hz, 1H), 7.00 (d, J = 7.5 Hz, 1H), 4.21 (s, 1H), 3.04 (t, J = 7.8 Hz, 1H), 2.74 (d, J = 17.9 Hz, 1H), 2.51 (dd, J = 17.8, 3.6 Hz, 1H), 2.25 (s, 3H), 2.15 - 2.07 (m, 1H), 2.05 (dd, J = 12.1, 3.8 Hz, 1H), 1.90 (dq, J = 14.3, 8.1 Hz, 1H), 1.83 - 1.73 (m, 1H), 1.64 (ddd, J = 13.5, 7.5, 5.5 Hz, 1H), 1.40 (d, J = 12.1 Hz, 1H), 1.07 (s, 3H). ¹³C NMR (CDCl₃, 125 MHz): δ 221.6, 177.0, 146.2, 137.2, 135.4, 129.2, 128.6, 120.7, 55.8, 51.4, 50.7, 50.0, 48.2, 39.1, 34.6, 23.0, 21.8, 19.7. HRMS(ESI): m/z calc. for C₁₈H₂₁O₃ [M+H]⁺: 285.1491, found: 285.1492. HRMS(ESI): m/z calc. for C₁₈H₂₀O₃Na [M+Na]⁺: 307.1310, found: 307.1312.