The Michael or conjugated addition is a nucleophilic reaction of a carbanion to an a,�-unsaturated system, and it is one of the most powerful methods to generate carbon-carbon bonds. To improve reaction scope and efficiency, there has been a steady survey of chemical reactive including organocatalysis, transition metal and lantanide mediated reactions for the past decade. In line with these efforts, herein we disclose an unprecedented cascade of conjugate additions that afford tricyclic compound 5  resembling the core of the anticancer natural product Enmein.  The simplicity and readily availability of the inexpensive starting materials render this reaction an ideal ground for studying its mechanism and further derivatization for SAR studies.  Our current working hypothesis and future asymmetric version for this project will be presented.

Study of novel nucleophilic cascade formation of tetraethyl 6-oxo-4,4a,8,9-tetrahydro-1H-benzo[c]chromene-2,2,10,10(3H,6H,10aH,10bH)-tetracarboxylate

244th National Meeting (2012)

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