Isoquinoline Alkaloids Research 1972–1977

Benzylisoquinoline alkaloid biosynthesis in opium poppy

“…1) (Amann et al 1984;Gesell et al 2011;Matsushima et al 2012). However, berberine and other modified protoberberines have generally not been reported in opium poppy (Shamma and Moniot 1978;Shulgin and Perry 2002). Moreover, protoberberines in which the berberine bridge has formed between the N-methyl and the 6′ carbons, as opposed to the 2′ position (i.e.…”

The oxidation of 3-alkylhomophthalimide derivatives by dioxygen in alkaline media and Bischler-Napieralski reactions of cleavage-cyclisation products

“…The preparation of lactonic amide precursors for Bischler-Napieralski cyclisation reactions that can lead to phthalide-isoquinoline alkaloids 24 is frequently troublesome. 25 It is clear that our new procedure provides a straightforward route to amidophthalides which, if the benzyl group in, for example (2 or 6), was replaced by a b-arylethyl residue, could function as key intermediates in Bischler-Napieralski cyclisation reactions en route to analogues of phthalideisoquinoline alkaloids.…”

Étude des Hernandiacées. XII. Dimères aporphine–benzylisoquinoléine originaux isolés de Hernandiapeltata

“…I1 est connu que la (+) rtticuline conduit, via un couplage oxydatif intramoltculaire, a de nombreuses structures monomtriques (2,3). Or rtcemment nous avons pu isoler de Hernandia peltata Meissner trois alcaloi'des dimkres qui constituent le premier exemple connu d'un couplage oxydatif intermoltculaire de deux unitts dtrivtes de la (+) rtticuline (4).…”