Neue Synthese von (−)-(R)-Cembren A, Synthese von (+)-(R)-Cembrenen und (+)-(S)-Cembren

✍ Scribed by Imre Farkas; Hanspeter Pfander

• Book ID: 102256417
• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: German
• Weight: 437 KB
• Volume: 73
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19900730721

✦ Synopsis

Novel Synthesis of (−)‐(R)‐Cembrene A, Synthesis of (+)‐(R)‐Cembrenene and (+)‐(S)‐Cembrene

A novel synthesis of (−)‐(R)‐cembrene A ((−)‐3) was developed using the Sharpless epoxidation for the introduction of the chiral center. Furthermore, the synthesis of (+)‐(R)‐cembrenene ((+)‐4) showed that this cembranoid must have the (R)‐configuration and not, as previously reported, the (S)‐configuration. Selective hydrogenation of (+)‐4 afforded (+)‐(S)‐cenibrene ((+)‐5).