Volume 33, Issue 8
Natural Products
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ChemInform Abstract: Chiral Base Route to Cyclic Polyols: Asymmetric Synthesis of Aminodeoxyconduritols and Conduritol F.

Simon E. de Sousa

Simon E. de Sousa

Dep. Chem., Univ. York, Heslington, York YO10 5DD, UK

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Peter O'Brien

Peter O'Brien

Dep. Chem., Univ. York, Heslington, York YO10 5DD, UK

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Christopher D. Pilgram

Christopher D. Pilgram

Dep. Chem., Univ. York, Heslington, York YO10 5DD, UK

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First published: 22 May 2010

Abstract

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ChemInform Abstract

Ring-opening of the meso-epoxide (II) in the presence of a chiral base provides the chiral allylic alcohol (III) as key intermediate for aminodeoxyconduritols (V) and (VII). To demonstrate the utility of the enantioselective epoxide-opening conduritol F tetraacetate (X) is prepared from the isomeric allylic alcohol (VIII).

chemical structure image

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