Organic Letters 2006-05-25

In pursuit of pestalotiopsin a via zirconocene-mediated ring contraction.

Shuzhi Dong, Gregory D Parker, Takahiro Tei, Leo A Paquette

Index: Org. Lett. 8(11) , 2429-31, (2006)

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Abstract

[reaction: see text] An asymmetric route from the epimeric beta-hydroxy esters 4 and 5 to the densely functionalized (+)-10 and (-)-10, respectively, is described. Either cyclobutanol can be made available as the predominant product. The levorotatory antipode has been transformed into the advanced intermediate 21 bearing side chains destined to become incorporated into the cyclononene ring of the title compound (1).