ChemInform Abstract: Synthesis, anti‐GABA Activity and Preferred Conformation of Bicuculline and Norbicuculline Enantiomers.

Abstract

Synthesis, anti-GABA Activity and Preferred Conformation of Bicuculline and Norbicuculline Enantiomers. -The title compounds (VII) and (IX) are prepared using the Bischler-Napieralski cyclization. (+)-Bicuculline (IX) is 70 times more potent than its enantiomer as an inhibitor of GABAA receptor binding and 900 times more potent than (+)-norbicuculline (VII) at pH 5. -(KARDOS, J.; BLANDL, T.; LUYEN, N. D.; DOERNYEI, G.; GACS-BAITZ, E.; SIMONYI, M.; CASH, D. J.; BLASKO, G.; SZANTAY, CS.; Eur.

Concise synthesis of (R)-reticuline and (+)-salutaridine by combining early-stage organic synthesis and late-stage biocatalysis

“…In contrast, herein, we report a late-stage biocatalysis strategy in a 6–7-step chemo-enzymatic sequence for the synthesis of ( R )-reticuline ( R )-1 and its promorphinan product (+)-salutaridine (+)-3 ( Scheme 1E ), respectively, which are crucial intermediates for the morphinan/opioid synthesis. (+)-Salutaridine (+)-3 is of interest as it is a partial agonist at the GABA/benzodiazepine receptor complex, 46 a partial MOR agonist, 47 and also due to its use as anti-HBV agent. 48 The herein used strategy includes the transformation of a lignin-derived feed stock (24) towards the natural intermediate 1,2-dehydroreticuline 2.…”