Fig. 3: Synthesis of O-tbutyldiphenylsilylmenisdaurilide (23). | Nature Communications

Fig. 3: Synthesis of O-tbutyldiphenylsilylmenisdaurilide (23).

From: Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core

Fig. 3: Synthesis of O-tbutyldiphenylsilylmenisdaurilide (23).The alternative text for this image may have been generated using AI.

Reagents and conditions: (a) 16 (0.2 equiv), 17 (0.1 equiv), TBSCl (2.0 equiv), iPr2EtN (1.2 equiv), THF, –40 °C, 99% (95% ee); (b) VO(OEt)3 (0.05 equiv), TBHP (4.0 equiv), CH2Cl2, 0 °C to 23 °C, 98%; (c) DMP (1.25 equiv), CH2Cl2, 23 °C; SiO2, 94%; (d) TBDPSCl (1.2 equiv), imidazole (1.2 equiv), DMAP (0.1 equiv), CH2Cl2, 0 °C to 23 °C, 95%; (e) ZnBr2 (5.0 equiv), H2O (5.0 equiv), CH2Cl2, 50 °C, 83%; (f) diethylphosphonoacetic acid (2.0 equiv), EDCI (2.0 equiv), CH2Cl2, 23 °C, 96%; (g) K2CO3 (5.0 equiv), 18-crown-6 ether (5.0 equiv), THF, 0 °C, 61%. TBS tbutyldimethylsilyl, TBHP tbutyl hydroperoxide, DMP Dess–Martin periodinane, DMAP 4-dimethylaminopyridine, EDCI 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.

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