What question did this study set out to answer?

The aim is to develop a concise method for synthesizing (±)-mesembrine using Bi(OTf)3 as a catalyst.

March 25, 2026

Concise Telescopic Total Synthesis of (±)-Mesembrine via Bi(OTf) 3 -Catalyzed Generation of a Quaternary Center

Key Points

The aim is to develop a concise method for synthesizing (±)-mesembrine using Bi(OTf)3 as a catalyst.
Conducted Bi(OTf)3-catalyzed annulation of methyl enol ethers with methyl vinyl ketone.
Utilized a one-pot telescopic protocol for synthesis without isolating intermediates.
Employed mild reaction conditions to tolerate various enol ethers.
Achieved products with yields up to 95%.
Successfully synthesized (±)-mesembrine with an overall yield of 31%.
Obtained (±)-mesembrine in 30% yield using a streamlined method.

Abstract

We describe a Bi(OTf)3-catalyzed annulation of methyl enol ethers with methyl vinyl ketone, providing rapid access to α-branched aldehyde quaternary carbon frameworks under mild conditions. The reaction tolerates diverse enol ethers, affording products in up to 95% yield. Application of this method enabled the total synthesis of (±)-mesembrine in 31% overall yield via a key α-quaternary aldehyde intermediate. Furthermore, a streamlined one-pot telescopic protocol enabled the direct synthesis of (±)-mesembrine in 30% yield without isolating intermediates.

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Concise Telescopic Total Synthesis of (±)-Mesembrine via Bi(OTf) 3 -Catalyzed Generation of a Quaternary Center

Key Points

Abstract

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