Journal of Organic Chemistry 2010-04-16

Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels-Alder reaction.

Marko Weimar, Gerd Dürner, Jan W Bats, Michael W Göbel

Index: J. Org. Chem. 75 , 2718-2721, (2010)

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Abstract

Starting from Dane's diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert-Dane route in 24% total yield. The key step is an enantioselective Diels-Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.