Work

Gram‐Scale Access to (3,11)‐Cyclotaxanes—Synthesis of 1‐Hydroxytaxuspine C

Year: 2025

Type: article

Abstract: Herein, we present the semisynthesis of complex taxane diterpenoid 1-hydroxytaxuspine C. Starting from cheap and abundant 10-deacetylbaccatin III, a scalable and robust route was developed, enabling an unprecedented gram-scale access to the intricate (3,11)-cyclotaxane scaffold. In addition, this represents the first synthetic access to C1-hydroxylated cyclotaxanes. The natural product is synthesized in 17 steps, with the reactions being performed on decagram-scale up to an advanced intermediate, establishing the scalability of this approach.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202506245

Authors: Philipp Schoch, Yulia Krivolapova, Fabian Schneider, Lu Pan, Tanja Gaich

Institutions: University of Konstanz, Shanghai University of Traditional Chinese Medicine, Longhua Hospital Shanghai University of Traditional Chinese Medicine, Leibniz University Hannover

Language: English

Topic: Biological Activity of Diterpenoids and Biflavonoids

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funder: European Research Council