Fig. 6: Total synthesis of (‒)-lucidumone [(‒)−1]. | Nature Communications

Fig. 6: Total synthesis of (‒)-lucidumone [(‒)−1].

From: Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Fig. 6

Reagents and conditions: a HCl (2 M in ethyl acetate) (10.0 equiv), DCM, ‒78 °C, then DMP (2.0 equiv), NaHCO3 (10.0 equiv), RT, 80%; b KF (5.0 equiv), H2O2 (20 equiv), KHCO3 (1.6 equiv), MeOH-THF (v:v = 1:1), 50 °C, 91%; c 2-nitrophenylselenocyanate (1.2 equiv), Py (1.2 equiv), PBu3 (1.2 equiv), H2O2 (24 equiv), THF, 50%; d Fe(dbm)3 (0.1 equiv), PhSiH3 (10 equiv), EtOH, RT, 65%; e AlCl3 (10 equiv), 1-dodecanethiol (20 equiv), DCM, RT, 70%.

Back to article page