Author: Nawasreh, Mansour M.

Source: Current Organic Chemistry, Volume 13, Number 4, March 2009 , pp. 407-420(14)

Publisher: Bentham Science Publishers

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)

Document Type: Research article

DOI: http://dx.doi.org/10.2174/138527209787582286

Publication date: 2009-03-01

Related content

• In this: publication
• By this: publisher
• In this Subject: Organic Chemistry
• By this author: Nawasreh, Mansour M.

Website © Publishing Technology. Article copyright remains with the publisher, society or author(s) as specified within the article.

• Terms and conditions
• Privacy policy
• Information for advertisers