The total synthesis of (+/-)-fortucine and a revision of the structure of kirkine.

Aurélien Biechy (1) , Shuji Hachisu (1) , Béatrice Quiclet-Sire (1) , Louis Ricard (2) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique
2 DCPH - Laboratoire Hétéroéléments et Coordination

The total synthesis of the natural product fortucine relies on a radical cascade process initiated by the generation of a nitrogen-centered (amidyl) radical (see picture). The procedure is concise, and tin-free, as well as stereo- and regioselective. This synthesis has enabled the correction of the structure of kirkine, and the strategy represents a general and rapid entry into the galanthan framework.

Domaines: Chimie organique

Aurélien Biechy, Shuji Hachisu, Béatrice Quiclet-Sire, Louis Ricard, Samir Z. Zard. The total synthesis of (+/-)-fortucine and a revision of the structure of kirkine.. Angewandte Chemie International Edition, 2008, 47 (8), pp.1436-1438. ⟨10.1002/anie.200704996⟩. ⟨hal-00969141⟩