The goal of this project is the asymmetric total synthesis of the natural product cyanocycline A, a member of the
naphthyridinomycine family, which was isolated in 1982 from the fermentation broth of Streptomyces flavogriseus
strain No. 49 and is a broad spectrum antibiotic.
Our approach makes use of two hetero Diels-Alder reactions which have not been sufficiently reported in the
literature. The first is a hetero Diels-Alder involving an imine with a stereogenic element not at the nitrogen to
induce diastereoselectivity. The second is a hetero Diels-Alder with a 2-azadiene and a quinone. This synthesis
should contain 17 steps and be accomplished using only a minimal number of protecting groups. Compared to the
synthesis by Fukuyama (32 steps) and the formal synthesis by Garner (22 steps), this synthesis would be
substantially shorter.