Synthesis of (IR)-(+)-cis-chrysanthemic acid

✍ Scribed by J.S. Yadav; Sudha V. Mysorekar; A.V.Rama Rao

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 562 KB
• Volume: 45
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89196-1

✦ Synopsis

A synthesis of (lR)-cis-chrysanthemic acid from (R,R)-tartaric acid is described. The diol 8 was corn&x&i to the mono MEM protected cqmpourd 8b. Dehflration of the tertiary alcohol us@ meihanesulfonyl chloride-triethylamine-DMAP aml treatment of the resultir\g product with lithium in liquid ammonia affotied 10. lhe diazoester of 10 was .Wjected to intramolecular cyclopropamtion usiw a soluble copper complex to obtain 12. Cleavage of the MEM ether, deh@ration of the tertiary alcohol followed by reductive cleavage with lithium in liquid ammonia gave the title compcud.