Three-Component Multi-Catalytic Enantioselective Oxa-Michael/Aldolization Sequence and Application to (+)-Yashabushitriol Synthesis

Céline Sperandio (1) , Jean Rodriguez (1) , Adrien Quintard (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

By a selective three‐component multi‐catalytic sequence, amino‐catalyzed oxa‐Michael addition of oximes to α,β‐unsaturated aldehydes has been combined with a copper‐catalyzed decarboxylative aldolization. This one‐pot procedure enables the rapid construction of functionalized ketodiol scaffolds in 85 to 94% ee. Simple reduction of both the resulting oxime and ketone functions delivered the corresponding 1,3,5‐triols of interest in a minimum of steps while considerably limiting waste generation. This methodology has been applied to the shortest (4 steps) synthesis of (+)‐yashabushitriol, highlighting the synthetic potential of this new multi‐catalytic sequence.

Mots clés: Enantioselective synthesis; multi-catalysis; polyols; catalysis; natural product synthesis; cascade

Domaines: Chimie organique; Catalyse

Céline Sperandio, Jean Rodriguez, Adrien Quintard. Three-Component Multi-Catalytic Enantioselective Oxa-Michael/Aldolization Sequence and Application to (+)-Yashabushitriol Synthesis. European Journal of Organic Chemistry, 2020, 2020 (17), pp.2493-2496. ⟨10.1002/ejoc.202000185⟩. ⟨hal-02568139⟩