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

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 alpha -position in the alpha -hydroxyl lactone moiety of pyranoindolizine is important for the antitumor activity. This...

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Bibliographic Details
Published in:Symmetry (Basel) 2015, Vol.7 (1), p.43-52
Main Authors: Odagi, Minami, Watanabe, Tatsuya, Nagasawa, Kazuo
Format: Article
Language:English
Subjects:
Anticancer properties
Bearing
camptothecin
Chirality
CHP
Cumene hydroperoxide
Derivatives
Lactones
organocatalyst
pyranoindolizine
Ureas
α-hydroxylation
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Summary: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 alpha -position in the alpha -hydroxyl lactone moiety of pyranoindolizine is important for the antitumor activity. This paper deals with enantioselective oxidation of the alpha -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.
ISSN:2073-8994
2073-8994
DOI:10.3390/sym7010043