 A Diels-Alder/retro Diels-Alder approach has been utilised in synthetic procedures towards the synthesis of a range of polycyclic heterocycles and the homoerythrina alkaloid comosidine. Chiral anthracene auxiliary 1 successfully controlled the enantioselectivity of Grignard addition or reduction to form cycloadducts 2, with addition of the nucleophile only on one face of the carbonyl. Intra- and intermolecular Friedel-Crafts reactions of aromatic nucleophiles with N-acyliminium ions prepared from maleimide cycloadducts were also successful. Enantioenriched products were liberated by cycloreversion.

Asymmetric synthesis of polycyclic heterocycles and application to the synthesis of comosidine

239th National Meeting (2010)

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