Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels− Alder Reaction

M Weimar, G Dürner, JW Bats…

Index: Quinkert, Gerhard; Grosso, Michael del; Bucher, Astrid; Bats, Jan W.; Duerner, Gerd Tetrahedron Letters, 1991 , vol. 32, # 28 p. 3357 - 3360

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Citation Number: 32

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