An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction

✍ Scribed by Michael H. Wu; Eric N. Jacobsen

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 184 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00192-5

✦ Synopsis

An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiane monoepoxide with TMSN~ catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen functionalization affords 2, thus completing a formal synthesis of balanol in 31% overall yield.