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. 2024 Nov 25;15(12):2225–2230. doi: 10.1021/acsmedchemlett.4c00510

Scheme 1. Synthesis of 2′-Me Meayamycin D.

Scheme 1

Conditions: (a) diisobutylaluminum hydride (DIBALH), CH2Cl2, −78 °C, 2 h; then (b) 9, KOtBu, tetrahydrofuran (THF), −78 °C to rt, 20 h, 52% (E:Z = 6:94); (c) NaOH, MeOH, 0 °C to rt, 16 h, quant.; (d) 10, HATU, diisopropylethylamine, CH2Cl2, 0 °C to rt, 42 h, inseparable mixture; (e) methacrolein, nitro-Grela catalyst, 50 °C, 20 h, 39% for 2 steps; (f) Ph3PCH3Br, KOtBu, THF, 0 °C to rt, 18 h, 78%; (g) 7, nitro-Grela catalyst, dichloroethane (DCE), 50 °C, 8 h, 8%; (h) DIBALH, THF, −78 °C, 1.5 h, 68%.