Work

Chemoenzymatic Total Synthesis of Lansai B

Year: 2025

Type: article

Abstract: Lansai B is an indole alkaloid whose biosynthesis is not yet elucidated. However, utilizing nature's tools enabled the stereoselective formation of this unique framework, first by providing the substituted tryptophan as starting material and later in the scaffold-building step forming the pyrroloindole motif. For the latter, the C3-methyltransferase from Streptomyces griseoviridis (SgMT) is employed for the diastereoselective methylation. Investigating the scope of the enzyme proved that introducing a bromide in the 5-position was ideal for the synthetic endeavor. With this, the stage was set for the synthesis of lansai B, introducing the prenyl group late via a Suzuki coupling.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202500740

Authors: Marcel Schatton, Mona Haase, Julia Tenhaef, Catharina Gronkowsky, Stephan Noack, Jörg Pietruszka

Institutions: Forschungszentrum Jülich, Heinrich Heine University Düsseldorf

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funders: Bundesministerium für Bildung und Forschung, European Regional Development Fund