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.

Subjects

DIELS-Alder reaction; CHEMICAL reactions; ANHYDRIDES; MALEIC anhydride; AMINES; IMIDES

Publication

Russian Journal of Organic Chemistry, 2003, Vol 39, Issue 1, p57

ISSN

1070-4280

Publication type

Academic Journal

DOI

10.1023/A:1023490528591