Preliminary Study of the Total Synthesis of Bao Gong Teng A Analogs Using 8-Benzyl-2-oxo-8-azabicyclo[3.2.1]oct-3-ene-6-endo/exo- and 7-endo/exo-carbonitrile

Olivier Chavignon (1) , Stéphane Rézel , François Estour (2, 3) , Damien Canitrot (4) , Elena V. Bejan Voinea , Jean-M. Chezal , Claire Lartigue (5) , Yves Blache (6) , Alain Gueiffier (7) , Gérard Dauphin , Jean C. Teulade

1 Etude Métabolique des Molécules Marquées
2 Secobra
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
4 IMoST - Imagerie Moléculaire et Stratégies Théranostiques
5 LURPA - Laboratoire Universitaire de Recherche en Production Automatisée
6 MAPIEM - Laboratoire Matériaux Polymères Interfaces Environnement Marin - EA 4323
7 N2Cox - Niche, Nutrition, Cancer et métabolisme oxydatif

The use of four cycloadducts from the Katritzky reaction for subsequent preparation of Bao Gong Teng A analogs was studied. We show that the reduction of 2-oxo-8-azabicyclo[3.2.1]octanes (1-4) to alcohols allows the 2-exo/endo isomerism to be exploited. The 7-endo compound (4) also yielded azatricyclo[5.2.l.04,8]decanone (12) from alcohol (11). When the nitrile was converted into an acetyl group, 6-endo products (13) and (14) were isornerized to 6-exo. Trimethylsilyloxy derivatives (13-18) ultimately yielded 2-hydroxy-azabicyclooctethanone (22-24). These results afford an approach to the synthesis of the 6-exo 2-endo, 7-exo 2-exo and 7-exo 2-endo isomers of Bao Gong Teng A.

Domaines: Chimie; Sciences du Vivant [q-bio]

Olivier Chavignon, Stéphane Rézel, François Estour, Damien Canitrot, Elena V. Bejan Voinea, et al.. Preliminary Study of the Total Synthesis of Bao Gong Teng A Analogs Using 8-Benzyl-2-oxo-8-azabicyclo[3.2.1]oct-3-ene-6-endo/exo- and 7-endo/exo-carbonitrile. Heterocycles, 1999, 51 (5), pp.989-1002. ⟨10.3987/COM-98-8447⟩. ⟨hal-02375738⟩