Ring Closing Metathesis Directed Synthesis of (R)-(−)-Muscone from (+)-Citronellal

✍ Scribed by Vijayendra P Kamat; Hisahiro Hagiwara; Tomoko Katsumi; Takashi Hoshi; Toshio Suzuki; Masayoshi Ando

• Book ID: 104202724
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 125 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00333-1

✦ Synopsis

AbstractÐA concise and simple synthesis of the valuable perfumery ingredient (R)-(2)-muscone 1 has been achieved through ring closing ole®n metathesis (RCM) aided macrocyclization protocol as the key step. Commercially available starting material (R)-(1)-citronellal 3 has been employed as a building unit in preparing the acyclic diole®nic substrate 16, which in turn was exposed to bis(tricyclohexylphosphine)benzylideneruthenium dichloride catalyst 2 to afford the cyclic RCM reaction product 17 in 78% yield. Catalytic hydrogenation of 17 furnished enantiomerically pure (R)-( 2)-muscone 1.