Stereospecific Synthesis of trans-5,6-Dihydropyridinones

Abstract

An efficient synthesis of trans-5,6-dihydropyridinones bearing a heteroatom (Br, OH) at C-5 has been achieved. The formal synthesis of (±)-epiquinamide and (±)-homopumiliotoxin 223G has also been accomplished through the formation of (±)-trans-1-hydroxyquinolizidin-4-one.

Key words

aza-Diels-Alder reaction - trans-5,6-dihydropyridi­nones - trans-1-hydroxyquinolizidin-4-one - epiquinamide - homopumiliotoxin 223G

References

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13

Crystallographic data (excluding structure factors) for compounds 4, 5, 6, 10, 11, and 12 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 796324-796329 as well as their corresponding CIF files. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].