Tetrahedron: Asymmetry

An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry

MG Banwell, S Chand, GP Savage

文献索引：Banwell, Martin G.; Chand, Satish; Savage, G. Paul Tetrahedron Asymmetry, 2005 , vol. 16, # 9 p. 1645 - 1654

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被引用次数: 19

摘要

The title natural product (−)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3, 5-dimethoxy-4-(methoxymethoxy) cinnamyl alcohol with the AD-mix-β to give triol (1R, 2R)-1-(3′, 5′-dimethoxy-4′- methoxymethoxyphenyl)-2, 3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These ...