Fig. 4 | Nature Communications

Fig. 4

From: Total synthesis of cyrneines A–B and glaucopine C

Fig. 4

Synthesis of the tricyclic compound 23. Reagents and conditions: (a) OsO4 (4 mol%), NaIO4 (5.0 equiv), pyridine (3.0 equiv), dioxane/H2O (v/v = 5:1), 80 °C (80%); (b) EtMgBr (1.1 eqiuv, 1.0 M in THF), −78 to 40 oC, overnight, then K2CO3 (2.0 equiv), MeI (5.0 equiv), and DMF were charged in situ, 55 oC, 10 h (72%); (c) PCC (4.0 equiv), NaOAc (4.0 equiv), celite (ca. 130 wt%), rt, 6 h (82%). THF tetrahydrofuran, DMF N,N-dimethylformamide, PCC pyridinium chlorochromate

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