Total syntheses of aplysin and debromoaplysin using a diastereoselective, sulfur mediated radical cyclisation strategy

✍ Scribed by David C Harrowven; Matthew C Lucas; Peter D Howes

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 126 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00768-6

✦ Synopsis

Total syntheses of two marine sesquiterpenes, aplysin I and debromoaplysin 2, are described. The key step involves a diastereoselective, sulfur mediated radical cyclisation of diene 5 to 7 which simultaneously creates the stefically demanding aplysin skeleton and establishes the relative configuration of the three contiguous stereogenic centres.