DIELS-ALDER REACTION OF LIGUSTILIDE GIVING LEVISTOLIDE-A AND TOKINOLIDE-B

Authors
OGAWA Y MORI Y MARUNO M WAKAMATSU T
Citation
Y. Ogawa et al., DIELS-ALDER REACTION OF LIGUSTILIDE GIVING LEVISTOLIDE-A AND TOKINOLIDE-B, Heterocycles, 45(10), 1997, pp. 1869-1872
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
10
Year of publication
1997
Pages
1869 - 1872
Database
ISI
SICI code
0385-5414(1997)45:10<1869:DROLGL>2.0.ZU;2-1
Abstract
Naturally occurring levistolide A (1) and tokinolide B (2) were first synthesized by a Diels-Alder reaction of ligustilide (3) under the sev eral reaction conditions. The dimer (2) was converted into the thermod ynamically stable dimer (1) at 200 degrees C. The calculation of HOMO and LUMO of 3 was also carried out by MNDO/PM3 method to explain the r egioselectivity.