Catalytic asymmetric synthesis of febrifugine and isofebrifugine

✍ Scribed by Shū Kobayashi; Masaharu Ueno; Ritsu Suzuki; Haruro Ishitani

• Book ID: 104260940
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 201 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00142-2

✦ Synopsis

Antimalarial alkaloids, febrifugine (1) and isofebrifugine (2), were synthesized from simple achiral starting materials using tin(lI)-catalyzed catalytic asymmetric aldol reaction and lanthanide-catalyzed aqueous three-component reaction as the key steps. These unambiguous total syntheses revealed that the absolute configurations of febrifugine and isofebrifugine were not (2'S, 3'R) and (2'R, 3'R) as reported previously but (2'R, 3'S) and (2'S, 3'S), respectively.