Journal of the American Chemical Society 2012-04-11

Formal synthesis of (±)-methyl rocaglate using an unprecedented acetyl bromide mediated Nazarov reaction.

Philip Magnus, Wesley A Freund, Eric J Moorhead, Trevor Rainey

Index: J. Am. Chem. Soc. 134(14) , 6140-2, (2012)

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Abstract

To date the prototype Nazarov cyclization of a cross-conjugated pentadienone to the core structure of the rocaglate natural products has not been successful (9 into 12). It has been found that this conversion can be achieved by the use of acetylbromide in excellent yield and results in a strategically very direct route to these antitumor agents.© 2012 American Chemical Society