4673-12-5Relevant articles and documents
Amidyls in radical cascades. The total synthesis of (±)-aspidospermidine and (±)-13-deoxyserratine
Callier-Dublanchet, Anne-Claude,Cassayre, Jér?me,Gagosz, Fabien,Quiclet-Sire, Béatrice,Sharp, Lisa A.,Zard, Samir Z.
, p. 4803 - 4816 (2008/09/21)
Concise routes to aspidospermidine and 13-deoxyserratine are described, hinging on a cascade starting from an amidyl radical and allowing the construction of the key indolizidine cores in one step.
The 1-Aza-Cope Rearrangement
Wu, Pei-Lin,Chu, Min,Fowler, Frank W.
, p. 963 - 972 (2007/10/02)
The 1-aza-Cope rearrangement of azavinylcyclohexene derivatives were investigated.It was observed that an N-acyl substituent on the 1-aza 1,5-diene provides a sufficient driving force for this normally contrathermodynamic process.Although simple derivatives have high activation energies proceeding in relative low overall yield, a methoxy substituent at C-4 of the aza diene as well as its incorporation into strained bicyclic ring systems facilitates the 1-aza-Cope rearrangement.Because the aza diene precursors are readily available by using the Diels-Alder reaction with acrolein derivatives, this process has synthetic potential for the preparation of nitrogen heterocycles.This scheme is illustrated with the preparation of a hydrolulolidine providing a formal total synthesis of (+/-)-aspidospermine.
