LEE, DU and IWASA, K and KAMIGAUCHI, M and TAKAO, N and WIEGREBE, W (1991) DEGRADATION OF SOME PHTHALIDEISOQUINOLINES WITH ETHYL CHLOROFORMATE-STEREOCHEMICAL ASPECTS. CHEMICAL & PHARMACEUTICAL BULLETIN, 39 (8). pp. 1944-1948. ISSN 0009-2363,
Full text not available from this repository.Abstract
Treatment of phthalideisoquinolines such as alpha- (1) and beta-narcotine (2) as well as beta- (3) and alpha-hydrastine (4) with ethyl chloroformate (ECF) at room temperature afforded, via the chloro-carbamates, the corresponding diastereomeric carbinols with high stereoselectivity. Instrumental analyses of each diastereomeric pair indicate that the major isomers derived from alpha- and beta-narcotine as well as from alpha- and beta-hydrastine are enantiomers of each other. The absolute configuration of the major carbinol 6a from alpha-narcotine (1) was determined by X-ray analysis. The probable difference between the reaction course of alpha- and beta-narcotine is discussed. On the other hand, treatment of alpha-narcotine with ECF under reflux furnished Z-(8) and E-(9) enol lactones, while only the Z-isomer 12 could be isolated from the degradation of beta-hydrastine (3) even at room temperature.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RHOEADINE; ALPHA-NARCOTINE; BETA-NARCOTINE; ALPHA-HYDRASTINE; BETA-HYDRASTINE; ETHYL CHLOROFORMATE; DIASTEREOSELECTIVITY; ENANTIOMER; DIASTEREOMERIC CARBINOL; ENOL LACTONE; X-RAY ANALYSIS; ABSOLUTE CONFIGURATION |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:46 |
| URI: | https://pred.uni-regensburg.de/id/eprint/54930 |
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