Development of Chemistry-Based Screening Platform for Access to Mirror-Image Library of Natural Products by Taro Noguchi

Author:Taro Noguchi
Language: eng
Format: epub
Publisher: Springer Singapore, Singapore

1-(2,4-Dihydroxyphenyl)-2-{[(S)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl]oxy}ethan-1-one (12d)

According to the procedure described for the preparation of 12b, compound 10d (500 mg, 1.16 mmol) was converted into compound 12d as pale yellow solid (483 mg, 72%) (Fig. 2.17): mp 86–87 °C; −3.9 (c 1.11, CHCl3); IR (neat): 3350 (OH), 1626 (C=O); 1H NMR (500 MHz, CDCl3) δ 0.84–0.87 (m, 12H), 1.04–1.61 (m, 21H), 1.24 (s, 3H), 1.73–1.85 (m, 2H), 2.08 (s, 3H), 2.14 (s, 3H), 2.18 (s, 3H), 2.58 (t, J = 6.9 Hz, 2H), 4.92 (s, 2H), 6.36 (dd, J = 8.9, 2.6 Hz, 1H), 6.42 (d, J = 2.9 Hz, 1H), 7.51 (d, J = 9.2 Hz, 1H), 12.40 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 11.8, 11.9, 12.8, 19.7 (2C), 20.6, 21.0, 22.6, 22.7, 23.8, 24.4, 24.8, 28.0, 31.1, 32.7, 32.8, 37.3, 37.4 (2C), 37.5, 39.4, 40.1, 74.0, 75.0, 103.8, 108.1, 111.8, 117.8, 123.2, 125.7, 127.6, 130.9, 147.7, 148.3, 163.0, 165.3, 198.0. HRMS (ESI) calcd for C37H57O5 (MH+): 581.4201; found: 581.4207.

Fig. 2.17Structure of 12d

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