Synthesis of (±)-
trans-chrysanthemic acid from (±)-
trans-caronic acid via ester of (±)-1'-hydroxy-dihydro-
trans-chrysanthemic acid by the dehydration with
p-toluene-sulfonic acid was attempted. However, the attempt was found to be unsuccessful giving a compound believed to be methyl methyl 2, 6 dimethylhepta-3.6-diene-5-carboxylate upon dehydration.
A cleavage upon cyclopropane ring was confirmed by deriving the acid obtained by the hydrolysis of the above ester to already known 2, 6-dimethyl-heptane-5-carboxylic acid.
Analogous mode of dehydration and cleavage upon the ester of (±)-2, 2-dimethyl-3-
trans-hydro-xylbenzyl-cyclopropane-l-carboxylic acid was also observed to give 1-phenyl-4-methyl-penta-l, 3-diene-3-carboxylic acid. On the other hand, (±)-
trans-caronic acid being derived to (±)-1'-oxo-2'-hyd-roxy-dihydro-
trans-chrysanthemic acid, the synthesis of (±)-
trans-chrysanthemic acid from (±)-
trans-caronic acid became possible using (±)-1'-oxo-2'-hydroxy-dihydro-
trans-chrysanthemic acid as a relay substance.
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