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Updated: Jan 31, 2026

Organic Structure-directing Agent-free Synthesis for *BEA-type Zeolite Membrane
Published on: February 22, 2020
Stereoselective Total Synthesis of Eburnane-Type Alkaloids Enabled by Conformation-Directed Cyclization and
Guang Li1, Cyril Piemontesi1, Qian Wang1
1Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
Abstract:
Controlling the cis C20/C21 relative stereochemistry remains an unsolved issue in the synthesis of eburnane-type indole alkaloids. Provided herein is a simple solution to this problem by developing a unified and diastereoselective synthesis of four representative members of this class of natural products, namely, eburnamonine, larutensine, terengganensine B, and melokhanine E. The synthesis features the following key steps: a) an α-iminol rearrangement transforming the 3-hydroxyindolenine into spiroindolin-3-one, b) a highly diastereoselective conformation-directed cyclization leading to the melokhanine skeleton with the desired C20/C21 cis stereochemistry, and c) either an aza-pinacol or an unprecedented α-aminoketone rearrangement converting spiroindolinone back into the indole skeleton.
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