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Gram-Scale Access to (3,11)-Cyclotaxanes-Synthesis of 1-Hydroxytaxuspine C.

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.

SUBMITTER: Schoch P 

PROVIDER: S-EPMC12377431 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature

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Gram-Scale Access to (3,11)-Cyclotaxanes-Synthesis of 1-Hydroxytaxuspine C.

Schoch Philipp P   Krivolapova Yulia Y   Schneider Fabian F   Pan Lu L   Gaich Tanja T  

Angewandte Chemie (International ed. in English) 20250716 35

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  ...[more]

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