Total Synthesis of the Callipeltoside Aglycon

✍ Scribed by Ian Paterson; Robert D. M. Davies; Rodolfo Marquez

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 109 KB
• Volume: 113
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3757(20010202)113:3<623::aid-ange623>3.0.co;2-v

✦ Synopsis

The callipeltosides were isolated by Minale and co-workers from the shallow-water lithistid sponge Callipelta sp., collected off the east coast of New Caledonia. [1a,b] Callipeltoside A (1 in Scheme 1, obtained in 1.4 Â 10 À4 % yield) was found to inhibit in vitro the proliferation of KB and P388 cells (IC 50 values of 11.26 and 15.26 mg mL À1 , respectively). Results indicate this activity to be cell-cycle dependent, blocking proliferation in the G1 phase, highlighting callipeltoside A as a putative, mechanism-based lead. [1a] Similarly, callipeltosides B and C, differing only in the sugar portion of their structures, also exhibited marked cytotoxic activity.