β Scribed by Silvia von Angerer; Erwin von Angerer; Reinhard Ambros; Wolfgang Wiegrebe
No coin nor oath required. For personal study only.
Degradation of (->a-narcotine (5). (-)-p-narcotine (6), and (-tP-hydrastine (7) with ethyl chloroformate (ECF) affords the chloro-urethans 9 and 18, respectively. Diastereomer 9-1 is easily hydrolyzed to the hydroxy-urethan 10, whilst 18 is converted to the methoxy-analogue 19. The stilbene lactone 11 is obtained from 9-1 by treatment with DBU, the analogous stilbene 17 arises already when 7 is reacted with ECF. -Hydroxy-urethan 10a phenylogous a d o 1is split by OHto aldehyde l3 and to meconine (14). LiAlqreduction of 10 yields the stereochemically homogenous trio1 IS, which is cyclized to diastereomers of the 3-phenyl-isochroman 16 under acidic conditions. Ringoffnung von Phthalidisochinolin-Alkaloiden durch Chlorameisensjiureeth ylester Der Abbau von (-)-a-Narkotin (5). (-)-p-Na&otin (6) und (-)+-Hydrastin (7) mit Chlorameisemiiureethyhylester (ECF) fiihrt zu den Chlomrethanen 9 bzw. 18. Das Diastereomer 9-1 reagiert leicht zum Hydroxyurethan 10, 18 zum Methoxy-halogen 19. Chlomthan 9-1 bildet mit DBU das Stilbenlacton ' 9-R P 4 -*) Part of the PhD-thesis S. von Angerer, n6e Prior, Regensburg, 1980. **) Dedicated with warm regards to Prof. Dr. J. Suuer, Regensburg, on the occasion of his 60. birthday.
π SIMILAR VOLUMES
The reaction of indoles (A) with superoxide ion resulted in ring cleavage to give o-formyl and o-acylaminoketones -(A) or N-acylanthranilic acid (s) and ring expansion yielding 2-quinolones (3). All reactions are chemiluminescent