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Communication | Regular issue | Vol 45, No. 10, 1997, pp.1869-1872
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7893
Diels-Alder Reaction of Ligustilide Giving Levistolide A and Tokinolide B

Yoshimitsu Ogawa, Yoshikazu Mori, Masao Maruno, and Takeshi Wakamatsu*

*Central Research Laboratory, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki, 300-11, Japan


Naturally occurring levistolide A (1) and tokinolide B (2) were first synthesized by a Diels-Alder reaction of ligustilide (3) under the several reaction conditions. The dimer (2) was converted into the thermodynamically stable dimer (1) at 200 °C. The caluculation of HOMO and LUMO of 3 was also carried out by MNDO/PM3 method to explain the regioselectivity.