An enantiospecific approach to thapsanes from R-carvone: synthesis of (−)-thaps-8-en-5-ol

✍ Scribed by A Srikrishna; K Anebouselvy; T.Jagadeeshwar Reddy

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 156 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01107-2

✦ Synopsis

The ®rst enantiospeci®c synthesis of a thapsane, containing three contiguous quaternary carbon atoms, is accomplished starting from R-carvone. An intramolecular alkylation and an intramolecular diazoketone cyclopropanation reaction were employed for the stereo-and regiospeci®c generation of three contiguous quaternary carbon atoms present in the thapsane framework.