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

Abstract

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.