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

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

Abstract read

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Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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3 · Its place in the literature

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1 citing paper in PubMed.

Gram-Scale Access to (3,11)-Cyclotaxanes-Synthesis of 1-Hydroxytaxuspine C.Angewandte Chemie (International ed. in English) · 2025
Article

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5 · Who and what money

Authors and funding

5 authors.

Philipp SchochDepartment of Chemistry, University of Konstanz, Universitätsstrasse 10, 78464, Konstanz, Germany.ORCID https://orcid.org/0009-0003-2621-826X

Yulia KrivolapovaDepartment of Chemistry, University of Konstanz, Universitätsstrasse 10, 78464, Konstanz, Germany.

Fabian SchneiderResearch Center for (Bio-)Synthesis of Active Small Molecules in Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China.

Lu PanDepartment of Chemistry, University of Konstanz, Universitätsstrasse 10, 78464, Konstanz, Germany.

Tanja GaichDepartment of Chemistry, University of Konstanz, Universitätsstrasse 10, 78464, Konstanz, Germany.ORCID https://orcid.org/0000-0002-6793-1374

Funding

European Research Council 101003072

6 · The paper itself

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.

Indexed as

Complex taxanesNatural productsPhotochemistryTaxane diterpeneTotal synthesis

Identifiers

PMID40518821

DOI10.1002/anie.202506245

PMCPMC12377431

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