Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis

Author(s): Grant S. Buchanan, John B. Feltenberger, Richard P. Hsung

Journal Name: Current Organic Synthesis

Volume 7 , Issue 4 , 2010


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Abstract:

An aza-[3 + 3] annulation or formal cycloaddition strategy for constructing complex heterocycles, chiefly alkaloids, is reviewed here. This annulation involves a Knoevenagel-type condensation of α,β-unsaturated iminium salts with vinylogous amides or urethanes followed by a 6π-electron electrocyclic ring-closure. Both the inter- and intramolecular aza-annulation pathways illustrated here constitute a stepwise formal [3 + 3] cycloaddition in which two -bonds are formed in addition to a new stereogenic center adjacent to the heteroatom. This review describes our total synthesis efforts in the last ten years to unequivocally demonstrate that this aza-[3 + 3] annulation can serve as a powerful approach and a unified strategy in alkaloid synthesis.

Keywords: Alkaloid synthesis, Aza-[3 + 3] annulation, Formal cycloaddition, Heterocycle, A unified synthetic strategy

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Article Details

VOLUME: 7
ISSUE: 4
Year: 2010
Page: [363 - 401]
Pages: 39
DOI: 10.2174/157017910791414490
Price: $65

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