Abstract
Herein, we reveal an unprecedented domino annulation of N-benzyl-acrylamides with 1,3-dicarbonyls for the assembly of fused tricyclic alkaloid frameworks incorporating a spirocycle via an alkylation/dearomative ipso-annulation/Michael addition (desymmetrization) sequence. This conversion involves three carbon-carbon bond formations, generating four chiral carbons, including three quaternary carbon centers, in a single diastereomer in one pot under identical reaction conditions. The synthetic potential of this atom-economic method is illustrated by modifications of the functional groups present in the products obtained.
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