Application of an amidyl radical cascade to the total synthesis of (±)-fortucine leading to the structural revision 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

A radical cascade initiated by a nitrogen-centred (amidyl) radical was developed, allowing the rapid construction of galanthan frameworks. It was applied to a concise, stereo/regio-selective and tin-free total synthesis of the natural product (±)-fortucine. This in turn resulted in the correction of the structure of kirkine. © 2009 Elsevier Ltd. All rights reserved.

Aurélien Biechy, Shuji Hachisu, Béatrice Quiclet-Sire, Louis Ricard, Samir Z. Zard. Application of an amidyl radical cascade to the total synthesis of (±)-fortucine leading to the structural revision of kirkine. Tetrahedron, 2009, 65 (33), pp.6730-6738. ⟨10.1016/j.tet.2009.04.027⟩. ⟨hal-00951265⟩