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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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02375738
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Submitted on : Friday, November 22, 2019 - 10:38:59 AM
Last modification on : Saturday, September 19, 2020 - 3:37:03 AM

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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, The Japan Institute of Heterocyclic Chemistry, 1999, 51 (5), pp.989-1002. ⟨10.3987/COM-98-8447⟩. ⟨hal-02375738⟩

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