VONANGERER, S and VONANGERER, E and AMBROS, R and WIEGREBE, W (1992) RING-CLEAVAGE OF PHTHALIDISOQUINOLINE ALKALOIDS BY ETHYL CHLOROFORMATE. ARCHIV DER PHARMAZIE, 325 (7). pp. 425-431. ISSN 0365-6233,
Full text not available from this repository.Abstract
Degradation of (-)-alpha-narcotine (5), (-)-beta-narcotine (6), and (-)-beta-hydrastine (7) with ethyl chloroformate (ECF) affords the chloro-urethans 9 and 18, respectively. Diastereomer 9-I is easily hydrolyzed to the hydroxy-urethan 10, whilst 18 is converted to the methoxy-analogue 19. The stilbene lactone 11 is obtained from 9-I by treatment with DBU the analogous stilbene 17 arises already when 7 is reacted with ECF. - Hydroxy-urethan 10 - a phenylogous aldol - is split by OH- to aldehyde 13 and tc meconine (14). LiAlH4-reduction of 10 yields the stereochemically homogenous triol 15, which is cyclized to diastereomers of the 3-phenyl-isochroman 16 under acidic conditions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:44 |
| URI: | https://pred.uni-regensburg.de/id/eprint/54469 |
Actions (login required)
 |
View Item |
