Abstract
A synthesis of (IR)- cis -chrysanthemic acid from (R,R)-tartaric acid is described. The diol 8 was converted to the mono MEM protected compound 8b. Dehydration of the tertiary alcohol using methanesulfonyl chloride-triethylamine-D M A P and treatment of the resulting product with lithium in liquid ammonia afforded 10. The diazoester of 10 was subjected to intramolecular cyclopropanation using a soluble copper complex to obtain 12. Cleavage of the MEM ether, dehydration of the tertiary alcohol followed by reductive cleavage with lithium in liquid ammonia gave the title compound.
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