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Divergent Enantioselective Total Synthesis of (−)-Ajmalicine, (+)-Mayumbine, and (−)-Roxburghine C

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We report herein a divergent enantioselective total synthesis of (−)-ajmalicine, (+)-mayumbine, and (−)-roxburghine C. The synthesis employs Franzén’s organocatalytic reaction between N -acetoacetyl tryptamine and ( E )-5-hydroxypent-2-enal to generate a functionalized pentacyclic compound with high diastereo- and enantioselectivity. This intermediate serves as a versatile platform for accessing the three heteroyohimbine alkaloids. Notably, a diastereoselective intramolecular Pictet–Spengler reaction of methyl ketone and chemoselective reduction of β-amidoester to β-enaminoester were exploited for the synthesis of (−)-roxburghine C.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c00715

Authors: Vincent Goëlo, Qian Wang, Jieping Zhu

Institution: École Polytechnique Fédérale de Lausanne

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: École Polytechnique Fédérale de Lausanne