Novel Reactions in the Cephalostatin Series

Author(s): Mansour M. Nawasreh .

Journal Name: Current Organic Chemistry

Volume 13 , Issue 4 , 2009

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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)

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Article Details

VOLUME: 13
ISSUE: 4
Year: 2009
Page: [407 - 420]
Pages: 14
DOI: 10.2174/138527209787582286
Price: $58

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