TY - JOUR
T1 - Syntheses of Methyl dl-Jasmonate and Methyl dl-2-Epijasmonate
AU - Tanaka, Hideo
AU - Torii, Sigeru
PY - 1975/2/1
Y1 - 1975/2/1
N2 - Syntheses of methyl dl-jasmonate (1) and methyl dl-2-epijasmonate (2) from 3a,7a-cis-3a,4,7,7a-tetrahydro-lindanone (3a) are described. Efficient construction of the carbomethoxymethyl and cis-pentenyl moieties could be achieved by developing a successful method for a key step, the partial oxidation of aldehyde hemiacetal 6, prepared from 3a, to acid hemiacetal 7a. The methyl ester of 7a was converted to both 1 and 2 by different routes via the thioacetals 8b and 11, respectively.
AB - Syntheses of methyl dl-jasmonate (1) and methyl dl-2-epijasmonate (2) from 3a,7a-cis-3a,4,7,7a-tetrahydro-lindanone (3a) are described. Efficient construction of the carbomethoxymethyl and cis-pentenyl moieties could be achieved by developing a successful method for a key step, the partial oxidation of aldehyde hemiacetal 6, prepared from 3a, to acid hemiacetal 7a. The methyl ester of 7a was converted to both 1 and 2 by different routes via the thioacetals 8b and 11, respectively.
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U2 - 10.1021/jo00892a018
DO - 10.1021/jo00892a018
M3 - Article
AN - SCOPUS:0016630383
SN - 0022-3263
VL - 40
SP - 462
EP - 465
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -