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Development of Guanidine-Bisurea Bifunctional Organocatalyst Bearing Chirality at the Inner and Outer Sides of the Urea Groups, and Application to Enantioselective α-Hydroxylation of Pyranoindolizine Intermediate for Camptothecin Synthesis

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei city, Tokyo 184-8588, Japan
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Academic Editor: Svetlana Tsogoeva
Symmetry 2015, 7(1), 43-52; https://doi.org/10.3390/sym7010043
Received: 17 December 2014 / Accepted: 8 January 2015 / Published: 14 January 2015
(This article belongs to the Special Issue Asymmetric Catalysis)
Pyranoindolizine is a tricyclic structure found in various biologically active compounds, such as camptothecin (CPT) and its derivatives. In the case of CPTs, the chirality at the α-position in the α-hydroxyl lactone moiety of pyranoindolizine is important for the antitumor activity. This paper deals with enantioselective oxidation of the α-position in pyranoindolizine lactone, which corresponds at C20 in CPT, with cumene hydroperoxide (CHP) in the presence of newly synthesized guanidine-bisurea bifunctional organocatalysts bearing chirality on both the inner and outer sides of the urea groups. View Full-Text
Keywords: α-hydroxylation; pyranoindolizine; camptothecin; organocatalyst α-hydroxylation; pyranoindolizine; camptothecin; organocatalyst
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Odagi, M.; Watanabe, T.; Nagasawa, K. Development of Guanidine-Bisurea Bifunctional Organocatalyst Bearing Chirality at the Inner and Outer Sides of the Urea Groups, and Application to Enantioselective α-Hydroxylation of Pyranoindolizine Intermediate for Camptothecin Synthesis. Symmetry 2015, 7, 43-52.

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