Abstract
This work aimed at selective synthesis of analogues of cephalostatin 1, a highly anti-cancer marine natural product according to NCI measurements. We summarized here the work done in our laboratories of five years studying the selectivity of certain reactions of cephalostatin-like bis-steroidal pyrazines and hence, the biological activity variation. This study includes chemo-, regio- and stereoselective reactions of analogues starting from the symmetrical bis-steroidal diketone (3), which can be synthesized in a gram scale from the commercially available hecogenine acetate (1a). The following routes have been tested: the regioselective hydroboration of the exocyclic double bond at C-12, the regioselective F-ring opening of the spiroketals moieties, the chemo- and regioselective hydroboration of Δ14,15 double bond and finally, the chemo- and regioselective reduction of the carbonyl group at C-12.
Keywords: Novel Reactions, Cephalostatin, biological activity, hecogenine acetate (1a), hydroboration, bis-steroidal diketone (3)
Current Organic Chemistry
Title: Novel Reactions in the Cephalostatin Series
Volume: 13 Issue: 4
Author(s): Mansour M. Nawasreh
Affiliation:
Keywords: Novel Reactions, Cephalostatin, biological activity, hecogenine acetate (1a), hydroboration, bis-steroidal diketone (3)
Abstract: This work aimed at selective synthesis of analogues of cephalostatin 1, a highly anti-cancer marine natural product according to NCI measurements. We summarized here the work done in our laboratories of five years studying the selectivity of certain reactions of cephalostatin-like bis-steroidal pyrazines and hence, the biological activity variation. This study includes chemo-, regio- and stereoselective reactions of analogues starting from the symmetrical bis-steroidal diketone (3), which can be synthesized in a gram scale from the commercially available hecogenine acetate (1a). The following routes have been tested: the regioselective hydroboration of the exocyclic double bond at C-12, the regioselective F-ring opening of the spiroketals moieties, the chemo- and regioselective hydroboration of Δ14,15 double bond and finally, the chemo- and regioselective reduction of the carbonyl group at C-12.
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Cite this article as:
Nawasreh M. Mansour, Novel Reactions in the Cephalostatin Series, Current Organic Chemistry 2009; 13 (4) . https://dx.doi.org/10.2174/138527209787582286
DOI https://dx.doi.org/10.2174/138527209787582286 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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