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- Title
Synthetic Transformations of Higher Terpenoids: VIII. [4+2]-Cycloaddition Reactions of Lambertianic Acid.
- Authors
Kharitonov, Yu. V.; Shul'ts, E. E.; Shakirov, M. M.; Tolstikov, G. A.
- Abstract
The Diels-Alder reaction of lambertianic acid with maleic anhydride occurred in a stereoselective fashion and yielded diastereoisomeric (1R,2S,6R,7R)- and (1S,2R,6S,7S)-exo-adducts. The latter reacted with L-valinol to give the corresponding diterpenoid imides, 4-aza-9-oxabicyclo[2.2.1]dec-8-enes. Reactions of lambertianic acid with N-substituted maleimides in the presence of Lewis acids afforded diastereoisomeric adducts having both exo and endo configuration. Some transformations of the adducts were examined with a view to obtain cantharidin and dihydroisoindole analogs.
- Publication
Russian Journal of Organic Chemistry, 2003, Vol 39, Issue 1, p57
- ISSN
1070-4280
- Publication type
Academic Journal
- DOI
10.1023/A:1023490528591