Gram‐Scale Access to (3,11)‐Cyclotaxanes—Synthesis of 1‐Hydroxytaxuspine C
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.
Authors
- Philipp Schoch (ORCID: https://orcid.org/0009-0003-2621-826X)
- Yulia V. Krivolapova
- Tanja Gaich (ORCID: https://orcid.org/0000-0002-6793-1374)
- Fabian Schneider (ORCID: https://orcid.org/0000-0001-6651-1127)
- Lu Pan (ORCID: https://orcid.org/0009-0007-8994-6722)
Institutions
- Leibniz University Hannover (DE)
- University of Konstanz (DE)
- Shanghai University of Traditional Chinese Medicine (CN)
- Longhua Hospital Shanghai University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-06-16
- DOI
- https://doi.org/10.1002/anie.202506245
- Citations
- 2
- Primary Topic
- Cancer Treatment and Pharmacology
- Type
- article
- Field-Weighted Citation Impact
- 2.09
Funders
- European Research Council