127681-72-5

Upstream product

• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 100-39-0 benzyl bromide 
• 81706-69-6 (4R,trans)-2,2,α,α,α',α'-hexamethyl-1,3-dioxolane-4,5-dimethanol 

Downstream Products

• 127681-66-7 (4R,5S)-4-(2-benzyloxyprop-2-yl)-2,2-dimethyl-5-(1-propen-2-yl)-1,3-dioxolane 

Relevant academic research and scientific papers

SYNTHESIS OF (1R)-(+)-CIS-CHRYSANTHEMIC ACID

A synthesis of (1R)-(+)-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-DMAP 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.