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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Gram-Scale Access to (3,11)-Cyclotaxanes-Synthesis of 1-Hydroxytaxuspine C
Philipp Schoch1, Yulia Krivolapova1, Fabian Schneider2,3
1Department of Chemistry, University of Konstanz, Universitätsstrasse 10, 78464, Konstanz, Germany.
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.
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