EMAIL THIS PAGE TO A FRIEND

The Journal of organic chemistry

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


PMID 22283818

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-initiated Nazarov cyclization of a heteroaryl alkoxyallene. Full details of these two approaches are given, as well as the characterization of undesired reaction pathways available to the Nazarov cyclization product. A sequence of experiments that led to an understanding of the unexpected reactivity of this key intermediate is described, which culminated in the successful total synthesis of (+)-rocaglamide.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

SML0656 Rocaglamide, ≥96% (HPLC)
C29H31NO7