Total synthesis of (±)-rocaglamide via oxidation-initiated nazarov cyclization

JA Malona, K Cariou, WT Spencer III…

Index: Malona, John A.; Cariou, Kevin; Spencer, William T.; Frontier, Alison J. Journal of Organic Chemistry, 2012 , vol. 77, # 4 p. 1891 - 1908

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Citation Number: 32

Abstract

This article describes the evolution of a Nazarov cyclization-based synthetic strategy targeting the anticancer, antiinflammatory, and insecticidal natural product (±)-rocaglamide. Initial pursuit of a polarized heteroaromatic Nazarov cyclization to construct the congested cyclopentane core revealed an unanticipated electronic bias in the pentadienyl cation. This reactivity was harnessed in a successful second-generation approach using an oxidation- ...